Win 50,000 Frequent Flyer Miles (+ Die Empty + WDS 2014)

In this post: Win 50,000 Southwest Rapid Rewards Miles (comment to enter here)

A New Book You Should Read (get it here)

WDS 2014 Tickets Now Available (sign up here)


Win 50,000 Southwest Rapid Rewards Miles

A few weeks ago I began my latest Frequent Flyer Challenge, where I regularly attempt to earn 200,000 or more miles and points in a single round of credit card applications (without negatively impacting my credit score).

Another new card came out after I wrote the original post, and this one is from Southwest Airlines. Just by getting the card and meeting a $2,000 minimum spend, you earn 50,000 Rapid Rewards pointsβ€”enough for two flights anywhere in the Southwest network.

Personally, I think the Ink Bold and Ink Plus cards are even better than this new one. With each of them you’ll also earn 50,000 points, enough for two flights, and you can transfer these miles to United for many more options. Nevertheless, I decided to get this card myself, just because I already have the other two and I was applying for additional cards around the same time.

I don’t usually fly Southwest, so I don’t want the miles. Do you? I’d like to use them to book two free tickets for someone in our community, and you can put your name in the hat by posting a comment.

A Few Simple Rules

1. You can enter once by commenting in this post. Where will you go with two free tickets? Tell us. (Hint: here’s the route map.)

2. I’m the one hosting this giveaway, not Chase bank or Southwest. I’ll use the 50,000 points to book the tickets for you by November 1, 2013 based on your preferences and availability.

3. Those are all the rules.

Note: Southwest recently announced a big devaluation in their miles. Fortunately, this devaluation doesn’t kick in until Spring 2014, so you still have several months to use these miles or any others of your own. This also points to a key principle of travel hacking: miles are for spending! Don’t hoard them!


Southwest Card
Ink Plus Card
Ink Bold Card

Die Empty: A Book You Should Read

A lot of good books have been coming out recently. I recently enjoyed Kate Northrup’s Money: A Love Story and The Year Without Pants by Scott Berkun.

Another great new book just came out a few hours ago. Die Empty from Todd Henry is all about giving your all and doing your best work. I’ve known Todd for years, ever since first discovering his great Accidental Creative podcast while running on the beach in Ghana a long time ago.

The new book is both inspirational and practical. Here’s what I said about it for my back cover blurb:

“You have a limited number of days on Earth. This book sends an urgent message: make them count!”

Regular readers will know that I write about mortality from time to time, in particular in the free manifesto The Tower. As much as possible, I try to live and work with urgency, aware that when each day ends it will never return. Todd’s work exemplifies this value well. Check out the book!

WDS 2014: Tickets Now Available!

Speaking of urgency, yesterday we opened up the first round of ticket sales for #WDS2014, the greatest adventure of all time. Our team has been working hard in the early stages of planning. One of the questions that has guided us is: “How can we make a great experience better?”

We never want to slack off or take anything for granted. If you’d like to join us for an amazing experience next summer, please do! Ticket sales are now open. Once this round ends, we won’t have any more tickets until sometime in 2014.

OK, that’s a wrap!

I hope you all are very well.

Comment below if you’d like to win the 50,000 miles. Our biased judges and feline assistant will pick a winner (maybe two winners…) on Sunday night at 6pm PST.

UPDATE: Comments are closed! Our judges will choose someone based on all those great entries.


Image: Therefore

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    • Brandon says:

      Thanks for putting those miles out to the world, Chris! I fly southwest almost exclusivey because I have friends and family scattered across the South and East coast. I would use the points to visit them. Plus my best friends wedding is in LA in a few months. An expensive flight, so these miles would definitely help! Cheers!

    • Leigh says:

      I can travel-hack my way to a lot of places, but the place that I go the most often is also the most difficult. I’d use the miles to get from Chicago to Sacramento, where my boyfriend is in grad school. Southwest is one of the only airlines that offers direct flights between the two cities, and the other (United) is far more expensive. With two tickets, I could visit him once and he could visit me once. We don’t always know when we’ll get to see each other again, so having those tickets booked would be awesome.

    • Steve says:

      I don’t normally fly Southwest either, but I could put those miles to good use. There are a lot of places on the West coast I’d like to see. I haven’t made it over there very much so that’s probably where I’d go.

    • Andrew says:

      Thanks for being generous with your points – my wife and I would love to win! Would travel to Chicago-Midway for Thanksgiving with the tickets.

    • Meredith Jones says:

      I would go to Vegas, baby!

    • Thanks for this opportunity Chris. I am still working out the plan & kinks of my new site and these miles would help tremendously!!

    • Ashley says:

      Thanks for offering this Chris! I recently flew my first flight on Southwest and was really happy when they corrected my lack of knowledge of their seat claiming rules by helping up my place in line so I’d love to fly them again.

      I would go to Seattle early next year to visit my friends and explore a city I’ve always wanted to live in and then book a flight to Philadelphia to explore a new city for me. Then I’d visit my cousin and her son in PA as I’d love to get to know them more as a recent death in my family as shown me how important spending time with family is. It’s hard when I’m on the West Coast and they’re on the East Coat so the tickets would really help!

    • Leigh Anne says:

      I think we will just draw from a hat and see what adventures might await us. I love to fly.

    • Carl Sergio says:

      The easy answer is I’d fly out to WDS 2014!! I’d give the other flight to my brother so he could come too. We’ve been dying to go but haven’t been able to make it work yet- and I’ve never been to Portland! My favorite travel quote is “I haven’t been everywhere, but its on my list”.

    • Paul Gerald says:

      I would take my girlfriend to Boston so she can have one last visit with her great aunt, her dad’s only surviving sibling, and see the North End house where Auntie and Dad grew up. And I love Boston!

    • Richard says:

      I would visit a city on the west coast that I’ve never been to; thanks!

    • Rebecca Eichler says:

      My best friend is having a baby in February. I’d use the miles for my daughter and me to go visit them.

    • Jay Sanders says:

      I would go to Salt Lake City from Portland to visit family. I also want to mention a couple things. I love how you have Portland Pride. I live in Vancouver, kinda close. Mabye sometime I’ll run into you in Portland. I love your stuff. I bought your book. I got into flier miles a little over a year ago because I stumbled upon your Frequent Flyer e book. I bought it, learned all I could and earned almost a million miles and points since. Chris, thanks for all the info and inspiration. I tip my hat to you. Jay

    • Liz says:

      That’s really cool of you to give away your miles. I’ll throw my hat in the ring. I’d use the miles to finally make that trip to New York City that I’ve been trying to do forever.

    • Luke says:

      First, I’d try to convince my fear-of-flying wife that we HAVE to use these miles, or it would be just disrespectful. And if that works, we’ll figure out where to go. πŸ™‚

    • Nicole D says:

      I would fly from Seattle to visit my family in Utah. I haven’t seen them in over a year!

    • Jenn says:

      I’d 1. visit family in NY and 2. I’d finally get to Big Sky Country– have dreamt of Montana my whole life!

    • Libby Harris says:

      Thanks so much, how exciting! This would be an epic opportunity for me to spread my wings. It would be wonderful to travel over the holidays and new year to see snow (I’m in Texas). Also, I have a list of restaurants (Food Network, gets me every time) and landmarks (Travel Channel) I would love to check out. YIPPY! (fingers crossed here)

    • Barbie says:

      I have always loved to travel and I came from a traveling family
      via my Dad being a pilot in the Air Force, my brother a Delta Captain,
      and 2 sisters who were life long flight attendants for American and TWA!
      I love being in the air.

    • Carolina says:

      You are awesome Chris!
      I would use those miles for my dream new year’s in Las Vegas and to visit my friends in Portland.

    • Hao Tran says:

      Sacramento! To visit family.

    • CraigO says:

      I would fly to help the orphans. {{{{summons karma from the ether}}}}

    • Amy says:

      Hi there! Thanks for hosting this giveaway. I would use the miles to fly to Chicago! I’m a bridesmaid for a good friend, and I am looking for a way to fly there for both her wedding day and bachelorette celebration.

    • Natasha M. says:

      Southwest has always had a special place in my heart after traveling exclusively on the airline throughout college and getting fantastic deals! If I won your miles, I would visit San Diego for my birthday in December. It’s usually cold, overcast, or snowing in Chicago, so it would be amazing to actually see the sun and enjoy being outside. Plus, it’s always been my dream since I was little to have a birthday on a beach with friends!

    • Adam says:

      Thanks for the opportunity Chris! We live in the Portland area and I would love to take my wife on a trip to Charleston SC in celebration of our 22nd Wedding Anniversary. We missed doing a trip on our 20th as she was expecting a baby at the time.

    • Lacey says:

      By giving me these tickets you could help me celebrate my friend, my uncle, AND kick off my new West-Coast business! I would go visit my best friend, whom I haven’t seen in 3 years–she just recently got engaged. My uncle, also in Seattle, just GOT MARRIED to his partner of many, many years. AND I am planning in the next four months to launch the West Coast part of my coaching business. I couldn’t figure out HOW to get to Seattle to see my loved ones and start my business. This would be an amazing gift for my friend, uncle and me and my business. AONC, you are amazing for what you do and for offering these to us. Pick me!

      To sweeten the deal, I’ll do almost anything you want for advertising AONC on my trip to Seattle or back here in my DC home. Want a picture of me using your miles to get to take a picture of a goat on top of the original starbucks in Seattle? Done. No need to know why you have a thing for goats, it’s ok, I get it. Want me to create a flashmob that ends up spelling the letters AONC at a public landmark. Done. I don’t care it’s a little narcissistic of you. You’re worth it! Want a picture of your logo with Obama? I’ll make it happen you little world dominator, you

    • Taynia says:

      I need to make a trek from Raleigh over to Sacramento for my grandma’s 80th birthday bash. Last time we flew, I didn’t have to pay for my daughter as she was only one. Now she’s three. Paying to have the honor of begging a three year old to sit still for six hours is not my idea of a fun way to spend money. But we love granny πŸ™‚

    • What a great idea to share the miles you won’t use! I’d happily accept them to fly from Portland to Las Vegas in November, as I’ll be speaking at a business growth seminar for CPAs and haven’t purchased tickets yet.

      I picked up a ticket to WDS 2014 yesterday, and I’m very much looking forward to attending. I had no excuse for not attending the past two years, so I decided I don’t want to miss out on the shenanigans next year!

    • I would get a ticket to Chicago for the Gay Christian Network (GCN) Conference happening in January. I would give the second ticket away to someone who would like to go to the conference but can’t afford the travel expense (and work with GCN to make sure they get a scholarship for hotel/registration). As a recipient of a scholarship in the past, this would be an awesome way to give back!

    • Caleb says:

      Thanks for being so generous with your miles.

      I fly SW fairly frequently since I am based in PHX. My birthday is in October (15th) and I would love to get away with my longtime girlfriend. It’s my 35th and I want this to me a big year for me (after reading both your books this summer) and would love to kick it off in a place I love that provides lots of inspiration for me – Portland! We were there in May and I actually picked up “The $100 Startup” there at Powell Books. It would be fitting for me to return to kick off what I hope is a stellar year for me (plus Portland has the most amazing veg food!).

    • Laurie says:

      I’d fly to Norfolk, Virginia! I’ve just been able to trace my family ancestry to Virginia in the mid-1600s (yes, the 1600s, that’s not a typo) and would LOVE to see where my family started its US journey. p.s. your commitment to generosity continues to inspire!

    • Evan says:

      Thanks for being so generous Chris! I’d be using the miles to head from NYC to Austin to meet clients for my business!

    • Chandra Chase says:

      Hello Chris. What a great idea to share this treat. I have a little story as my entry to win:

      Travel is a treat…
      A dream to fly and depart can be so sweet
      one part hard work, one part retreat
      It’s on a journey that we meet… ourselves, the world and come to see, its more then just point A to B.
      Travel makes me complete.

      My husband and I has a baby a year ago and all the travel in our lives came to a halt. It’s in times of absence when you realize what is truly important. Travel fused our joys together. We’d go somewhere completely ridiculous and without reason to feel the joy of adventure again.

      Thank you for the contest!
      Chandra & James

    • Chris,

      I would love to take my Wife to Boston so she can see the East Coast for the first time and also where I grew up. I’ve been on the West Caost for 7 years now and it would be great to get back to Boston and have some Maine Lobster. I’ll even bring a few back to share with you.

      Thanks for the chance.

    • Kelly Kashas says:

      Chris, thanks for all your uplifting posts and continued generosity towards your fellow hacks! I would love to go to New Orleans with my husband for a romantic/ghost tour/gorge myself on food weekend!

    • Johnny Wu says:

      Hey Chris,

      I’m at the tail end of a 2 year stint living away from my girlfriend Sarah. We’ve been doing long distance (me in Boston, she in Denver) and I’ve been using your travel hacks to help earn miles to see her more often.

      These tickets would be used to surprise her in Denver for our anniversary. But anyways great book recommendation looking forward to reading it.

    • Katie Parise Neves says:

      Chris- My husband and I got married last August and were never able to take a honeymoon because we relocated to Texas for work and used all of our funds to travel home to New England for various wedding-related trips. We’d use 2 tickets to honeymoon (a year late) in Northern California…driving up the coastal highway and stopping to enjoy hikes & bike rides, camping, the Redwood Forest, vineyards, rugged beaches, dinner & a trolley ride in San Fransisco (and a run across that gorgeous bridge!), and a stop to visit my brother who is attending graduate school in Palo Alto. What an inspired idea to share your points! You have such a generous spirit.

    • Adam says:

      I would take my wife to Seattle! We’ve always wanted to go there!

    • Peter says:

      Very generous Chris. My wife and I would fly to Hartford to visit my family. Thanks for all your posts – very encouraging.

    • Christina says:

      This is so generous, Chris! I thought I’d put my name in the hat — I would use the tickets to fly from Chicago to visit my best friend since 8th grade in Salt Lake City (we’re in our late 20s now). We don’t get to see each other as much these days, and I’ve never been to SLC, so this would be great! Thanks!

    • Nate says:

      Thanks for inspiring! Heading to Argentina in less than a month (first vacation out of country)!!!

    • Kris says:

      Hi Chris! Thank you for this!

      With two tickets I would go to NOLA. Want to do a free workshop for the still vast amounts of people still displaced by Hurricane Katrina. Focus: using your creativity as a means to begin a livelihood that serves humanity, no matter their socio-economic status. To help them have hope and discover ways to bring in more income.

    • Ulyana Ivankiv says:

      What a great opportunity. I would definitely go back and visit my grandmothers in Kolomiya, Ukraine.

    • I’d take my non-conforming homeschooling photographer daughter to Albuquerque, rent a car, and do a borderland research trip for the novel I’m currently writing, The Girl Who Was Never Not Broken.

      We would have a blast and I know we’d come home with photographs and scenes and great memories from a southwestern mother-daughter road trip. πŸ™‚

    • Marcela FernΓ‘ndez says:

      I am marcela, from Colombia and I am currently living in SF. I a doing the gap year program of UNcollege. I drop out university and I am doing a documentary of alternative education projects so I will definately use the Southwest tickets to visit some of the projects around the US. It will be a great gift and contribution for our project in which we hope to help more educational deviant to find heir way and show the world that there are different ways o learning and specially of being your truer you: be happy

    • Janis says:

      I love Southwest. If I won the tickets I’d want to fly to one of Southwest’s destinations that I haven’t previously flown too such as Manchester, New Hampshire, Portland, Maine or Key West, Florida.

    • Jim Fleming says:

      Thanks for sharing…will donate to a child of your choice in Last Wish Foundation

    • Kami Rogers says:

      I would use the tickets to fly myself and my son to Baltimore. My father died when I was seven years old. I’m now 29 and I just recently met my siblings for the first time. I have a wonderful sister and brother. I was always an only child. My mother never remarried after my father died. So, it’s been wonderful getting to know these two beautiful people. They are the only people I know that are also related to my father. It’s a connection to him that I am so grateful to have found. They both live in the Baltimore area and I have only had the opportunity to travel there once to see them and my son has not met them yet. My son is also an only child and he has a couple of cousins there that I would love him to meet. It’s really just my son and I here and I want to give him that family. πŸ™‚ It would be a wonderful trip, especially if we could pull off a holiday time trip. Spending the holidays with extended family would be amazing.

    • Lauren Wong says:

      You’re awesome for offering these up to our Small Army of Remarkable People! My mom has wanted to take a road trip through San Fran, Portland (what what!), Seattle and Vancouver – so I would love to use the tickets to fly us there and rent an old VW van to trek it through the Northwest!

    • Jason Vought says:

      I would fly to Portland to visit the city I am planning on moving to.

    • Nikki D says:

      Muchas gracias, Chris, for hosting this contest! I am pretty much flexible as my dream would be to see fave Tame Impala in concert so California and Denver, Co would be awesome!! Heart Tame Impala!!

    • Jessica says:

      I think I’d visit New Orleans! Never been and have always wanted to visit.

    • Therese says:

      Thank you for offering this, Chris. I would use the tickets to take my sister to NYC to see theater, museums, the 9/11 memorial and many other sights. She battled breast cancer earlier this year and has had a few setbacks in her reconstruction and is a bit depressed. I think this would cheer her up. Anyway, love your blog/writing/ideas.

    • Marko Kujaca says:

      Hey Chris!

      I would fly from Chicago to San Francisco early December this year.
      I have an important event to attend to and i still have not booked my ticket.
      This prize would help cover the costs getting there.
      Many thanks.


    • Michael says:

      Thanks for the gift. I would use them right away going from Chicago to Panama City, FL. Then drive over to Gulf Shores, AL to spend time with great friends!

    • Ashley says:

      50,000 Southwest miles? Yes, please! That’s, like… 60 points per dollar. Or, after this spring, way less (boo). Fact: I’ve been to 38 of 50 states, but never Tennessee (or much of the South, for that matter). I’d go to Nashville. πŸ™‚

    • Ratana says:

      I’m 10 states away from having seen all 50, which is one of my ‘bucket list’ goals. I’d take the miles and fly East in the early fall (from LA to Hartford, CT). From there, I’d pick up a car and drive through Massachusetts, Rhode Island, Vermont, up to Maine and come back through New Hampshire. Boom! 4 states to go. Thanks for the opportunity and happy travels to all!

    • Sharon says:

      To Colorado, to visit friends I haven’t seen in 7 years and show my little one what mountains look like!!!

    • Tanya says:

      Thanks Chris – I’d send my daughter (12) to visit her (lonely) cousin in SF – who just started school. I’d send my son to visit a winter baseball clinic in FL.

    • Jillian Haggerty says:

      Chris -This is such a nice thing that you’re doing! I would love to take my husband to Seattle for his birthday!

    • Anthony says:

      My brother and I were raised by a single-mother in NYC. This is a woman whose priorities were 1. Be a good mother, 2. Be a good Mother, and 3. Everything else. Now that we’re older, it’s starting to sink in for her that we won’t always be around the house to offer company and spend time with her. Recently, she asked me to make her a Facebook account and she was so happy to connect with old friends. One of these rekindled friendships is with an old boyfriend in Florida with whom she had to break up with because their lives were going in different directions 20 years ago (her paying herself through college with two kids, etc.). They’ve been talking every day since then and it’s so cute to hear them chat over phone, giggling as they retell old stories. I haven’t seen her this happy in years. If I won these two tickets, I’d send my mother to Florida and show her that there’s still hope for love and living a good life with all the years she has left.

    • Julian Walker says:

      I am a big fan log the travel hacking cartel. I would use the tickets to allow my wife to visit her father who has Alzheimer’s. He has moments if lucidity still and I know he would enjoy the trip.

    • Pearse says:

      Hi Chris,

      Thanks for the opportunity. I live in Vermont so if (when πŸ™‚ I will I’ll fly out of Manchester NH or Plattsburg NY and head either to San Diego CA or Denver CO – depending on where my wife wants to go for vacation. We have three kids so getting two free flights would be fantastic!

      Thank you!


    • ben capozzi says:

      I’m terrified of flying, but for her birthday I promised my wife I’d get over it and we’ll start traveling together in some way other than interstates. So, of course we’d use the points to fly out to Portland for WDS 2014 since, by then of course, I’ll be a flying fool!

    • Kinji N says:

      With your tickets I’d book RT tickets from Portland to Albuquerque. I would take my 11 year old son (I’d have to do promo to accrue my RT, car rental I have points thanks to your site). We would first spend time with my Grandma in Northern NM. Since, the tickets would be paying it forward I’d be sure to pay forward to another. Hmmm.. probably volunteer at a Golf youth camp that the Director keeps inviting me to do and I’ve wanted to and will make happen. Ps I’m golf novice, its about the kids lol πŸ™‚ The last intention would be to find the business opportunity I’ve been dreaming about that connects me logistically between NW and SW. There is such beauty between both πŸ™‚ Just seeking the right idea. Thanks it’d be so great!

    • Amanda says:

      Thanks for sharing your the Southwest miles with us. I use Southwest exclusively to visit family and friends in the west, and for vacationing. I just got home from Portland, Oregon coast, and Bend. Beautiful state!

    • Erin says:

      I’d go to Pittsburgh, PA! Why on earth would one do that with no friends or family in the area? It’s been on my bucket list for ages to see Frank LLoyd Wright’s Fallingwater house, the magical home with a waterfall running through it. And a free ticket would silence my often overly objection-oriented “rational” brain removing the barriers to making the trip. To see it in autumn with the leaves changing? {swoon}

    • Hi Chris ~ Thanks for offering up these tickets! I would take my 10 year old son on a mother/son trip to the Big Easy. I had wanted to take him to Paris earlier this year and that trip didn’t work out. New Orleans is the next closest thing that doesn’t involve a passport. Merci!

    • Kym Witt says:

      I will use the miles to fly to Michigan for my daughter’s wedding shower in February, and to bring her home to Oklahoma for her shower here πŸ™‚ SOUTHWEST IS MY FAVORITE! Also, this wedding (and ALL THE EXPENSES involved…..sheesh) is the PERFECT time for us to try your “get a bunch of miles without ruining your credit score” strategy! Here’s to free miles!

    • Lauren C says:

      I would love to take my little sister on a girls’ trip to the west coast for some quality time and wine. We’ve been dying to get away for a weekend together, but money is tight and free flights would certainly help make it possible. Thanks!

    • Katy Joe says:

      This is an awesome opportunity…I would love to use the miles to travel to Sacramento, CA from Lansing, MI. I am looking to move out west, and have had such a hard time affording getting out there to find a place without the use of a reliable car and very much money. These miles would be incredibly helpful!

    • My husband and I would use the miles for our trip to Florida for his mother’s 101st birthday!

    • Chris Healy says:

      Cool deal Chris. I’ve been using your travel hacking advice for a few years now – last year I booked 15+ international flights with miles! Back in the states now I’ve leaned on ideas from $100 Startup to start a business which is now about 8 months old – and it’s all about helping. So…thanks for all that!

      If I won the miles I’d use them to fly my biz partner and myself to a professional conference (blogging+content strategy) in 2014.

    • sheri forell says:

      I think I would give the tickets to my daughter and her husband as they could use them for a trip to go see the Detroit Lions pay some where. They are loyal fans in California and would love to see them in person. Of course it would have to be in one of the cities that Southwest services.

    • Katie says:

      Thanks for the generosity, Chris!
      I would definitely use them to take a trip the most obscure and picturesque place Southwest offers. I would spend my time there continuing my passion for photography and sharing that with others. Whoever you gift them to is a fortunate one!

    • Scott Larson says:

      I would love to have these tickets for my wife to to fly from Milwaukee, WI. to see our son in San Diego, CA, I have had health issues that have stopped me from making any trips. He is along way from home. It would be even better if he flew from San Diego to Milwaukee, WI., then I could see him also. Thanks for being a Non- Conformist

    • Rhea says:

      I love Southwest! I would visit my daughter in Portland OR for Thanksgiving. It would be amazing.

    • Julie says:

      I love to travel… especially since I’m landlocked in Alaska! But it is very expensive from here, so I don’t get out often.

      I would take a nice long vacation with my family if I won~ We could visit family in the lower 48 that we haven’t seen in years… we would need to hit a lot of states to do that… Georgia, Colorado, California, Minnesota, and Texas are the main ones!

    • Jin Tran says:

      My boyfriend comes into Atlanta from Nepal for work once a quarter, and the next time will be in January. I currently live in San Francisco and would love for us to see each other within his two- to three-week window. We would use the tickets to do a round-trip for one of us.

    • Kinji N says:

      I’d book RT tickets from Portland to Albuquerque. I would take my 11 year old son (I’d have to do promo for my RT, car rental I have points thanks to your site). We’d 1st spend time with my Grandma in Northern NM. Then, I’d be sure to pay forward to another. Hmmm.. probably volunteer at a Golf youth camp that the Director keeps inviting me to do and I’ve wanted to and will make happen. Ps I’m golf novice, its about the kids lol πŸ™‚ Last intention would be to find the business niche I’ve been dreaming about that connects me between NW and SW πŸ™‚ Just seeking the right idea. Thanks it’d be so great!

    • Lisa Russell says:

      What an awesome opportunity! I’d love to use the tickets for myself and my boyfriend to travel from Chicago – Atlanta. This would allow us the opportunity to celebrate an early Christmas holiday with his family before heading to Argentina + Antarctica late December. We’re scraping everything we can together to make it to Antarctica as it will be my 7th continent before 30 – a lifelong goal met and wonderful way to celebrate the big 3-0.

    • Holly Winter says:

      I would love a plane ticket to fly from Denver to New York. Last week my older sister had a terrible shock — her house burned down. All people and pets got out safely, but they lost everything else. In the wake of every relic being taken from them, family is what’s left. Relationships remain.

      I have been reminded how important family is and really want to rush home so I can spend time time them.

      Usually I’m good at keeping enough money in savings so I can get home, if need be. But I’m just publishing my memoir (Launch party is on Oct 7th.) so all of my money has been funding my dream.

      Thanks for considering…..

      Holly Winter
      Denver, CO

    • Diane P says:

      Probably a trip to Indy to see Mom.

    • Lara Buelow says:

      Vielen Dank! This is so exciting.

      I would use the tickets to visit a long-lost friend of mine in New Orleans. She has been asking me to visit her for years. She recently had a baby, so I would love to meet the new member of our tribe! Plus, we’ll stroll the Mardi Gras parades together with ice cold lemonade. (ideally). =)

    • Rebecca says:

      Never fear I would use the miles to visit friends in the Southwest that I have not seen in 10+ years. This would give me the excuse to take my daughter to meet her aunts and uncles.

    • Elyse says:

      I would fly from Seattle to the Bay Area to attend my 10-year college reunion, and bring my boyfriend so he can visit his brother and 3-year-old nephew, who are going through a divorce. I am an artist/coach, and I just signed up for WDS on Weds at 9am on the dot (along with my CWA mastermind group), so I am a little short on cash for travelling right now. Would love to attend my reunion, reconnect with amazing people, and spread the word about my adventures in world domination πŸ™‚

    • John Griffiths says:

      Thanks so much!

      Where would I go? Well I’ve given it some thought and I’d probably take my wife and disappear across to San Francisco. My dad took us there when I was a child and the place has always fascinated me. The place is so steeped in history we’d probably have to spend a couple of months exploring all it’s charms.

      Plus we’ll bring you back some treats.

    • How generous of you to offer this prize! I would take my 84 year old mother to Denver (Littleton) for Thanksgiving or Christmas to see her grandson and great grandsons (2) whom she hasn’t seen in 3 years. She would be thrilled and so surprised. Tickets are so expensive that time of year. Take care, Chris. ~connie

    • Jamie says:

      I love miles! With miles like this, I’d go visit my good friend in NYC who just had a baby girl! Thanks Southwest!

    • Morgan says:

      BUR-AUS-SEA-BUR – all music festivals, all the time!

    • Stephanie says:

      RDU –> MSY in December. I’ve never been to LA and reuniting with traveling friends that I met in London & Berlin last summer.

    • Kali Hodes says:

      With the 50,000 points I would fly out to Charleston, South Carolina. I am currently studying at the University of Kansas, in 2011 I studied abroad through a program called Semester at Sea and met my roommate Jackie. I enrolled in this amazing opportunity without knowing anyone else and ended up becoming best friends with my roommate. On Semester at Sea we circumnavigated the world whiling visiting 13 different countries, including Morocco, South Africa, India, Vietnam, China, Japan, Costa Rica, and Honduras. We had some great memories and still keep in touch. Jackie was proposed to last May and the wedding is in her hometown of Charleston. I would use the points to fly out to attend the wedding and see some of my study abroad friends that I haven’t seen in two years. Thanks!

    • Travis says:

      Ummmm… Portland!!!!

      Ohh yea! WDS 2014 here I come!
      Will be my first year and a free flight would truly dominate! Have been wanting to go from the beginning however, running a non-profit isn’t the best on the wallet! But I drank AONC Kool-Aid and there’s no turning back!

    • Jenny says:

      Chris you are AWESOME to give away such an offer. I would put those points into excellent use next month and go to St. Louis from NJ/NY. I quit my job back in July because it was draining the life out of me and honestly haven’t been happier since. Now Im a soccer coach for one of the best clubs in the country and am working to get all my licenses (I should have listened to my soccer coach years ago haha) I never thought I’d be able to say that I love my job and enjoy it very much – not only do I get to play soccer a sport I grew up playing but I help other young players, parents, communities and parent coaches learn to love soccer as well. It’s very rewarding πŸ˜‰ and with your help I can get some of 2 certifications that would help me be a better youth soccer coach

    • Pia Ghezzi says:

      WOW! Thanks for being so generous with your offer! I’d fly PDX-TPA now that the weather is cooler!

    • Andy Green says:

      That is awesome you are giving away free miles.
      If I win, I would go to Ft Lauderdale, FL so I can get some sun.

    • C Duke says:

      Hi! I would go visit my family in Indianapolis for the Christmas holidays with the miles! Thank you so much for all the great information.

    • Mike says:

      Would love to make it to San Francisco for the North Face 50 miler. Thanks Chris!

    • Bruce says:

      This is from the Miles to Go Dept.? As someone commented, use ’em while they’re hot, and before SWA devalues them.

    • Russell says:

      Nonstop from BWI – ABQ and back for next Summer, to visit my family. Southwest is the only airline that does the nonstop flight.


    • Brian Judd says:

      I have been talking up my love for Portland to my wife for so long, I would have to use them to to take her there. Besides, It’s been a while since I got lost in Powell’s bookstore.

    • Michael Henderson says:

      A very generous offer indeed! I would use the miles to fly from SoCal to New Orleans for Jazzfest/ It is the greatest music and culture festival in the country, perhaps even the world. Thank you for your kind offer.

    • Shaun McClure says:

      I would visit my family in Las Vegas. We moved back to the midwest and we miss them a ton! My daughter would be the most xcited to see Grandma and Grandpa!

    • Hey Chris, I would use the flights to:

      1.) Travel to Seattle, and spend some time in one of my favorite cities, and take a bus up to Vancouver where I have a friend who wants to show me around one. So it’d be a two for one benefit.

      2.) The other flight I’d want to travel to San Francisco…a city I have never visited, but because it’s one of the more expensive cities, it always gets put on the backburner when you count flight/hotels/etc. I would stay with a friend and coordinate the date of the flight with a San Francisco meetup. The meetup would be for Ramit Sethi’s Brain Trust group which is most active in NYC and San Francisco, so I would get some entrepreneurship benefit out of it as well.

    • Very generous to give those up. Southwest is my airline! I would use the tickets to visit my friend who just started Med school in NY and to visit my family in Colorado.

    • Barbara Vice says:

      I would love those miles, Chris. They would allow me to take the sabbatical I’ve been planning for a couple years now, and take it sooner (before my first grand-baby is born in April!). I would travel light and do the following:
      1. Visit my birthplace near Sacramento (never been)
      2. Swing by San Francisco for a minute or three.
      3. Rent a motorcycle and ride along Highway 1 from Monterey to Pismo Beach.
      4. Hang out on the beach along the way and reflect on all the awesomeness that is life.
      5. Hang out with a dear friend in Ojai.
      6. Visit my grandparents’ grave sites at Selma (never been)
      7. Visit my favorite uncle in Fresno (while he’s still healthy and fun and has wisdom to share).
      8. Visit cousins in Ripon and eat their award-winning BBQ.
      9. Return to Sacramento and a flight home … still a 50+ year old soon-to-be-grandma, but no doubt a changed one.
      Thank you for the chance to enter πŸ™‚
      ~ Barbara

    • I keep building trust in my life as much as I can each day.
      I see myself travel to a new place that comes to my mind at that time, to experience and learn whatever I need to learn and experience at that time.
      I want to achieve to be a person who is honest, who feels sincerely happy with the highest quality I define to myself by the end of my life, and on the last day of living in my life. I understand the last day could be an any day including today.

    • Tim says:

      Thank you Chris for your generosity in making this offer. I have put out an intention for free world travel, and winning these tickets would be a great start in having that intention met. I would go to Chicago to visit my parents, or use the tickets to fly them from Chicago to California for a visit. Thank you, thank you, thank you, Universe (and you too Chris)!

    • Rebecca says:

      After reading all the comments, I almost feel guilty for entering! There are SO many people in need of these tickets. I wish you had enough for everyone! I don’t have anyone sick or dying to visit. I don’t have a friend or family member who has just had a tragedy in their life. Can we start a fund for all these people? I am a single mom with a startup who hasn’t taken a vacation in over a year. But don’t feel sorry for me, because I’m grateful for the roof over my head, two healthy children and the opportunities at my door.

      Have an awesome day!!


    • Oh Wow Chris – I would use the free flights to get my husband and me to WDS, I bought my WDS ticket right after they went on sale…it would be my very first time to be in Portland, and of course my first time to WDS! I echo your support of the book Die Empty…as you know, my story, allows me to see the true reality behind life being too short and that tomorrow is never a guarantee.

      Thanks, as always for your generosity, and good luck to everyone who has entered!!

    • Matthew Rogers says:

      I would use the miles to say I’m sorry and I love you to my soon to be ex-wife. To have one last getaway with my best friend and partner before we go our separate ways. She’s always wanted to go to San Francisco and my birthplace of Monterey is very close too. Our divorce has been nothing but respectful and loving, and this trip would help us have closure and build momentum transitioning into the next chapter of our lives. Thank you for considering.

    • Marcela Fernandez says:

      I will use it to visit alternative education projects specially in Boulder and of I visit them I will be able to include them in eduKaction. My alternative education documentary

    • Kara says:

      Awesome offer – I’d use the tickets to visit a friend in Salt Lake City who moved away from DC to Utah with her husband and I miss her so much!

    • Crystal says:

      My boyfriend lives in Durham, so we’d fly from Raleigh-Durham to Boston to visit some friends. We’d definitely make a toast to you while we’re there. See you at WDS2014!

    • Robin says:


      New Orleans is my absolute favorite place in America. It used to be cheap to fly their from my homebase (boston) but lately the prices have gone up, so its harder to justify going lately. There’s nothing better than hanging out french street listening to Jazz and eating crawfish, except getting there on free southwest flights.

    • Krista says:

      I don’t have a sad or profound story… I would use the tickets to take a break from my job (that I’m working on leaving for my own creative project!!) and take my east-coast girlfriend to see Portland, Oregon (she’s never been anywhere on the west coast). She would love me very, very much for showing her this magical place and I would feel at home. Wanting to feel at home – that must count for something. Maybe everything.

    • Paul says:

      I’d use the miles to visit Tucson, AZ to see my parents. Mom had a stroke about a year ago, and I’d like to see her.

    • Ryan says:

      Long time lurker here. Would love to win those tickets to visit my buddy in Portland who introduced me to you in the first place.

    • Fon James says:

      Hey Chris, I LUV Southwest! My hubby, kids, and I live in Houston, TX (HOU) but we (hubby and I) are from Mississippi. We would use the Southwest tickets to fly into my hometown of Jackson (JAN) to spend Thanksgiving with our family! Hubs hasn’t been home since LAST Thanksgiving due to work and the last time I went was for baby shower and a funeral (err yeah). Our kids are age 2 and older so these two tickets would be a life saver for us because we otherwise will have to drive to Mississippi for Thanksgiving, as four plane tickets are out of budget. Imagine being in a car for 10 hours with a 2 year old and a 5 year old (who tends to act like a 2 year old sometimes). Flight time 1 hour and 10 minutes gate to gate. Car travel on Interstate I-10 during Thanksgiving travel days… about 10 or more hours (that’s with potty breaks and wilding out moments and all…and I am talking about me wilding out).

      So yeah, your gift of two tickets would allow us to fly HOME verses drive home, which would allows us more time to spend with our families and eat that good old southern Thanksgiving meal (fried turkey anyone). LOL.


      Please and thank you πŸ™‚


      JAN bound

    • Other airlines? Oh, I could make a dreamy list that includes Rome and Mexico City and Australia and Galapagos and about four dozen more.

      Southwest? Southwest miles would take me happily through the more pedestrian travel that is visiting my family. I live in Seattle; much of my family lives in the panhandle of Florida, which is often – especially around the holidays – an extremely expensive flight for what it is. Those miles would get me home to see my mom, who I don’t see often enough. And I’d be elated too.

      It’s not the grandest adventure, but it’s one of the most necessary ones in my life.

      Thanks for doing this!

    • Heather B. says:

      I’d go to Portland! I want to relocate to Bend, OR – one of the dog-friendliest cities where my dog treat business, Kanine Kitchen, would do great and I could add new hiking reports to my blog, Hiking With Heather! Thanks for the opportunity!

    • Mark says:

      Hey Chris,

      Just got through the Frequent Flyer Master and am on a points binge! Gonna be getting about 60,000 miles in a few months thanks to those tips and can’t wait to put them to good use on our trip up through Canada to Halifax and PEI.

      My wife and I would use the SW miles to finally get around to visiting a good friend of mine in Boulder, CO. His parents’ house burned down a year or so ago and since he was living out there already, they up and made a move out that way to start fresh. Hope you can help us out! Thanks man.

    • John O'Neal says:

      I would give the miles to my friend Mark. Mark is an amazing graphic designer who also has a stage 4 aggressive tumor in his brain. He was operated on two weeks ago and they have given him 12 to 18 months. This was very difficult news for him and his family. His attitude and the way he is handling this has been inspiring to me. He is just starting chemo and radiation this week. He lives in Denver which is a great South West hub, so I would let he and his wife decide where they wanted to go. Thanks for doing this Chris. Peace brother.

    • Ashley Maden says:

      You are amazing and generous!!!! I would use a ticket to fly from Reno to Portland next year to experience the World Domination Summit 2014 and the extra ticket would allow me to invite a friend to experience the awesomeness with me! I only discovered your website a couple weeks ago and I feel like my state of mind has already become filled with motivation and excitement and I can’t wait until WDS 2014! I bought the $100 start-up and I am very impressed with the book so far! This is the best website I have discovered in a long time and it is quite refreshing! Thank you for sharing your miles and hope to see you all at WDS 2014!!! πŸ™‚

    • Candace says:

      This is SO awesome of you to do this!! I’ve followed you for many years and just love what you’re doing and the message/information you’re spreading!! My husband and I have only had 2 vacations in our 7 1/2 years together, so I would use the tickets to take he and myself to either San Diego or Boston (depends upon the time of year!)

      Thank You for this opportunity!!!

    • Thom Butler says:

      I would go back to New Orleans, where I moved right before Katrina and then had to leave. It’s still my favorite city and I’d like to hear the music, taste the food, see my friends and maybe get to hear Peace Songs at St. Louis Cathedral.

      I would also go to Boston to visit my best friend, with whom I skype almost daily, but haven’t seen in the flesh in several years.

    • John Griffiths says:


      Thanks for the book info, just grabbed a copy.

    • There are two conferences I would absolutely love to attend this November. Both are on the east coast & I’m on the west coast of Canada. If I won the tickets I’d love to to use them to fly from Seattle (fairly close to home for me) to both of them, with possibly a little detour to visit some of my online friends, in real life, in between conferences. Wait, scrap that idea. If I won the tickets I’d want to book two flights for my parents to Arizona/Florida – my Dad hasn’t flown in 25 years and he loves going somewhere warm for the winter, but the drive is so very long. That’s what I’d really love to do. Thanks for the opportunity.

    • Natalie says:

      I think I would go to Italy! My goal (per my personal yearly review) is to go to AT LEAST 1 new country a year, and this year I managed to get a layover in Australia for a week but that would hardly count! I’m a graphic designer who loves art, art history, languages, and food so Italy has been on my bucket list for ages. Fingers crossed, it’s my next trip, my bags are already packed!

    • ashleigh says:

      I would go to Nashville. I love the vibe of the city & I’ve only been there once and only for one day. I’m dying to explore the city (& to go to the store of the American Pickers guys)!!!

    • Joel Hickenbottom says:

      Hi Chris,

      My wife and I just got married. In Feb. 2013, we met in Israel on Valentine’s Day (day of all days), at the Sea of Galilee (place of all places). We were on two different Holy Land Tours, but she was from Mexico City and I from California, so we returned to our homelands. Well, through Facebook, we began talking and then next thing I knew, I was in love and I went to visit her on May 30, 2012. I proposed to her right after Christmas in Big Sur, California, at the base of the McWay waterfall. Fast forward, we got married June 1st, 2013β€”one year after we officially began dating. Last week, her and I were just in Mexico sorting out her visa and now we are back in Cali. We want to move to Nashville, but just found out that tickets are $380-$400 of each of us! As newly-weds, we’d love to be able to get out there to find a home to rent, then fly back to California to begin the move, hopefully by November of this year!

      Thanks Chrisβ€”keep of the world-domination.

    • Courtney Cantwell says:

      What an amazing gesture! My husband and I would use the miles to fly back and forth between Wisconsin and California. In 2011, our son was born 15 weeks early, while I was on a business trip to San Jose (1lb, 14 oz at birth). He lived in the NICU for 89 days & during that time we made lifelong friends w/the angels who cared for him.

      Our big dilemma in life now is whether to stay in WI (where all of our family is) or move to CA so he can better know his birthplace. We’ve been averaging 2 visits/year (1 w/son, 1 adults only) but having these miles could help us show him how brilliant both the West Coast and the Midwest are. Then he can help us make the ultimate decision. Thanks Chris! Following your journey is inspiring, to say the least.

    • Rowan Hartin says:

      I’d fly to San Francisco to see my brother, who is having his first child in Nov. I’d love to see my first niece or nephew soon after their birth!

    • Elaine says:

      I’d go to Las Vegas! Although I have traveled all over the world I have never been there. Thanks for the contest!

    • Brian says:

      I would go to San Francisco. I’ve only been to California once in my life and never to San Francisco. Since I work in a technology-rich field, I’d love to see what the tech community is like there.

    • Ellen says:

      I would fly from Detroit to Houston to visit my new grandbaby due October 24th!

    • Caren says:

      It’s my 30th birthday in December and I’m determined to not spend it in a cubicle. But, we only have a few short days for the vacay and expenses are tight. These Southwest miles would be a godsend to go to San Diego or Austin. One, to brave the winter surf or the other to stuff my face with glorious vegan food. Postcards coming your way if I’m selected – and thanks!

    • Cristine says:

      I’d head out to Austin, where my family lives. Haven’t seen them for three years due to budget issues and it’s long overdue. Thanks for doing this!

    • Patricia Cooney says:

      Dear Chris,

      Thank you for this offer! I’d use the miles for my husband, Ken Moore, who is the co-executor of his darling, now deceased, father’s will. Ken’s dad lived in Twin Falls ID where Ken has been flying (via Boise on SW) for the past few years. He is now flying every month to Boise to handle the affairs of his father’s estate (translated: going through and distributing where wanted to brothers and sisters, or donating or recycling or shredding parental belongings from the beginning of time it seems.) Ken flies next on October 4 but has not purchased any tickets for the next months to come. This monthly trip to Boise/Twin Falls is ongoing until he is done and all matters concluded with the estate.

      Any help with the plane fare would be more than greatly appreciated by me, Ken and our budget.

      Finally I have a question: how can you buy a ticket for someone else like my husband with your miles? I have some miles on SW but when I went to try to buy Ken’s Oct. 4 ticket with my miles SW website said since my rewards were in my name I could not buy Ken’s ticket.

      Thanks again for your offer and for any insight you can give me on how to use my miles.
      Patricia Cooney

    • Andy says:

      As part of an ongoing and lifelong commitment to stay connected with siblings that are spreading around the country, I would use two tickets to fly from MSP down to Phoenix (hopefully this January) where my wife and I (and daughter) would join my sister, her husband and kids for some time to catch up!

    • Jackie says:

      I’d like to use them to fly my oldest friends to our wedding in the LA area at the end of the year. I know it’s going to be a stretch for their budgets so anything I can do to help them with costs would be great.

    • Peter says:

      Very cool idea Chris. And thanks for the podcast recommendation – if love to know what other podcasts you enjoy.

    • Micah says:

      Sometimes the problem with chasing a career you’re passionate about is getting stuck in a paygrade that leaves much to be desired. Unfortunately, a sense of fulfillment and contribution towards the greater good isn’t an accepted currency applicable towards airfare, which puts a significant damper on my ability to travel–a thing I enjoy doing very very much.
      If I had the tickets, I’d use one to fly back home to Texas for Baylor’s last football game on December 7 in Floyd Casey Stadium–the stadium I grew up cheering for them in–and the other I’d use next summer to fly to Spokane so I could drive to Montana and just play outside for a week.

    • Erin says:

      You’re missing out! Southwest points can be used for hotel stays as well as other things (including flight with other airlines). I use southwest points for everything. Because my husband uses them almost exclusively, I paid for much of a 2 week trip to Portugal with SW points. We flew USAir. 3 RT airfares, and 6 nights of hotels with airfare FREE!! I’m telling ya…
      However, when I win this 50,000 points? I would like to go to Aruba. Southwest flies there now and I’ve never been. πŸ™‚

    • Sarah says:

      As exotic as traveling to Seattle would be, that is where I would go!! I just learned last week that my sister/bestfriend/soul mate is pregnant with her first kid. I would love to see her as much as possible during her pregnancy. I would love to be there for her every step of the way. It’s to bad distance has to get in the way of that. What a generous thing you are offering to give away. Thank you!!

    • Hania says:

      I love your playfulness and generosity. I would take my sweetheart on a Mystery Date to Cape Cod. We moved to Portland a year and a half ago and I want to bring the Portland vibe to our family and friends on Cape Cod where we moved from. Have a glorious trip to whoever wins. May it be me!

    • Kirsten says:

      A former international nomad, I returned to the U.S. about five years ago to “settle down” and get a “real” job. Though I have long dreamed of living on the west coast, I initially settled on the east coast because of my then-partner’s work. We have since separated but I have not made the westward move because I let myself get into the trap that, as a traveller I had worked deliberately to avoid. Although I have a masters degree, I work in social service in a low-paying job–my paycheck is spent on basic expenses and I’ve not been able to save for a move. I would use the ticket to take a reconnaissance trip to Seattle to explore neighborhoods and do in-person informational interviews to help build a professional network and get the wheels turning to make this move happen!!

    • Hannah Bohart says:

      This is great! I fly Southwest several times a year to keep up with family. I would love to use these to take my mom back to Alaska, where we lived when I was little. We need to get to Seattle and can take it from there! Thanks for doing this!

    • Megan says:

      Chris, thanks so much for the offer to gift the miles! I’d take my wife on a weekend getaway to PDX. Neither of us have ever been to Oregon, but I hear it’s such an amazing state. It would also help me warm her up to the idea of coming with me to WDS next summer!

    • Amanda Senn says:

      I would send my parents to Napa Valley for their 35-year anniversary. They always talk about going but I know they will never break down and buy the tickets for themselves. They have given so much for our family and I would love to be able to treat them to a wonderful trip to celebrate their amazing love for each other.

    • Sherie LaPrade says:

      Chris, thanks so much for posting this contest! I’m a big fan of the Cartel, but had to quit for a while due to an extremely tight budget. I would love to win the tickets for my twin sister and I! We’d either use them to join my parents on their trip to Las Vegas next spring (also not in the budget for us…) or we’d fly out to Tahoe. Never been and we live in the south now and severely miss snow LOL! =D

    • Akirah says:

      I’d go to either Tucson or Portland. My mother-in-law lives in Tucson and there’s a chance I’ll be speaking at a conference there. So a ticket would get me there! If that speaking engagement doesn’t work out, I’d love to visit Portland. I’ve never been!

    • Shannon says:

      Thanks Chris for this generous and exciting opportunity! πŸ™‚ San Francisco would be my destination without a doubt. I love the city and I’d be thrilled at the chance to meet up with my fellow Connect with Anyone members who live in the Bay area. I could also really use a vacation as I’m overwhelmed with getting my new business off the ground. I just wish my feline sidekick didn’t deem traveling so distasteful.

    • Bob Burke says:


      Wow! You are an inspiration as you lead by example. If chosen by your illustrious feline selection committee as the lucky winner, I would use the two SWA tickets to fly from SJC to MSY to run the New Orleans marathon on my birthday, February 2nd.

      Thanks for the opportunity and the dream!



    • Sarah Kubishta says:

      I am originally from Oregon and recently moved to Texas. I would use the miles to visit my family back home in Oregon, and then use the second to visit either Boston or Chicago. Thank you for the opportunity!

    • Megan Cain says:

      Hi Chris-

      My sister has been having a rough time this past year (she recently broke up with her partner of 9 years) so if I won the miles I would surprise her with them. We’d take a sisters trip to anywhere of her choosing and I would pamper her like only a big sister can! We live in different time zones so I haven’t been able to support her as much as I would like. This would be a great chance for me to show her how much I love her and gift her with a little healing during this time of change in her life.

    • Tearei Locke says:

      Holy smokes, nice contest! :o) I would love to visit my nephew in Boise, maybe Las Vegas, and perhaps pay any balance forward!

    • Chris, thanks for the generous offer you’re making! I’ve been going through your Empire Building program and would reward myself for getting my business off the ground. I recently received my first payment from my first client! I’d take my husband with me to Baltimore to celebrate with good friends there. πŸ™‚ Thanks for all that you do to help everyone live unconventional lives!

    • Wade says:

      Take the wife to Denver. She’s never been to the mountains. Have to show her the beauty that resides there.

    • Joanne says:

      With two kids in college, one in Houston (Rice University go Owls an the other at Ohio State, go Bucks) and a husband who starts a 6 month contract in Houston (travel expenses on us) that companion pass is looking pretty good to me!

      What would I use the miles for? Los Angeles Houston, or maybe Columbus, or maybe with all the shuttling back and forth we are about to do much needed vacation!

      Thanks for your generosity πŸ™‚

    • Would love to fly Southwest to Phoenix. A good old HS buddy of mine lives north of there by an hour or so and he was unable to come to our 40th HS reunion last month and my wife and I have talked about jaunting down there for a few days. I’ve flow SE a number of times and really dig their style πŸ™‚

    • Marcus says:

      Usually travel is spurred by a reason, family event, work, etc. With your gratious offer, I would like to take a long weekend with my wife to randomly explore someplace new. Do / see something we have never done, meet some new people and maybe get some new ideas…. Thanks.

    • Amanda says:

      Thanks for this opportunity! We recently moved up to Portland, OR and my little one is missing her cousins in Phoenix.
      I’d use the miles to fly her back to PHX and spend Halloween with them! She’d have much more fun with all of the other kids around and we’d both get the battery recharge you get from being with your family over holidays πŸ™‚

    • AJ Sena says:

      I’d visit my dad in Texas.

    • Lori Wostl says:

      I would fly to an Art Retreat from Denver to Charleston (October) or if that doesn’t work an Art Workshop in S.CA in January and if that doesn’t work an Art Workshop on Whidbey Island (Sea-Tac) next July…are you noticing a theme here? I love away workshops but never allow myself the privilege of just going to one for fun. Thanks for the opportunity! and the fun game.

    • Christy says:

      Hi Chris, I would take my boyfriend, who is visiting from the Czech Republic, out to Portland to see my favorite side of the country πŸ™‚

    • Greg McAteer says:

      New Orleans! My wife and I were married 30 years ago in Biloxi Ms. We have talked many times of going back and make a NO, Biloxi, GA trip out of it. This would be the perfect tie in for it.

      Since that time we have married off 3 of our 5 children, each wedding gets more expensive. Our wedding was $20 and took about 15 min.

      Love your site!

    • Bob Gramley says:

      I have no aversion to flying Southwest nor east-west to return for that matter. A fear of flying refrains me; in actuality the fear of paying for the flying detains me. I would fly the Southwest to the Midlands of Chicago to rejoice in spirit with long β€˜lost’ family not recently visited to attend the marriage of a special niece, and aren’t they all, who kindly extended an invitation to the happening. Ah the brothers and sisters and nieces and nephews shall, much needed, revitalize my soul. I will write the story, may even make the movie…

    • Molly's Vote says:

      I would like to visit Ft. Lauderdale. I think I would completely, but lovingly, freak my friend out. We worked together for years, shared tea and tears. Then we both moved away from London. Social media doesn’t cut it. I need to see her and hug her and catch-up. What an amazing thing this air miles will do.

    • Danny says:

      The Art of Nonconformity Blog
      A Place For Sharing Knowledge And Experience
      Southwest Airline Miles Are Awesome

    • Cheryl LaPrade says:

      WOW! What a great contest – how generous of you! I would use these tix for me and my twin sister. We’ve never been to the west coast and would love to see either San Francisco or Seattle! =)

    • Would love to travel with your miles. Mostly because I can tell people Chris Guillebeau personally sent me on a trip!

    • Jenna Austin says:

      Your giving away free tickets? FO’ REAL? Sweet. That’s awesome!
      I’ll be turning 30 in October and have been wanting to tromp around New Orleans for a long time. Eating real gumbo, trekking through cemeteries, and having my fortune read sounds like a heck of a good way to break into a new decade!

    • Liz says:

      To WDS 2014!

    • John Pruyn says:

      I would take my wife and go to New Orleans. Went LSU in Baton Rouge and have not been back for a long time. 20 years! I would love to show my wife the great culture of that part of the country and the wonderful people!

    • Elisabeth says:

      This would be amazing! I’m heading to PHL soon, but haven’t booked my ticket yet. Fingers crossed! πŸ™‚

    • Amy Nieto says:

      Chris, The Libberator and rest of team. Thank you for oferring these miles. That’s awfully nice of you!

      If I were selected, I would pick a city in the US and fly my cousin in NYC there and I would fly there from PDX. we’re both going through some trying times in our lives (hellllooo early 30s) and it would be great to escape and have at least one expense taken care of. It hurts me to know she is sad and constantly being challenged with no break in sight. We need some girl time! Thank you!
      (Also loving all these stories posted here!!)

    • Jennifer Mc says:

      Thank you so much for this opportunity! I would take my husband for a couple’s trip to NYC. πŸ™‚

    • Josh says:

      Excellent article showing different options to racking up frequent flyer miles. You’ve definitely piqued my interest!

      Now, where would I want to go?

    • Anna says:

      Hi Chris! How inspiring of you to host this giveaway!

      I’m visiting my mom, who has an intellectual & developmental disability, on a regular basis (trying for 1x/month) for the next several months. I just returned home to CA from central Illinois after spending a month moving her out of her abusive husband’s home, bouncing around hotels other family members’ homes with her, while trying to find an amazing group home for her. I finally found the perfect group home for her, and went to court and successfully got a 2-yr restraining order against her husband.

      Now that she’s safe and happy and starting a new life at 67, I’m trying to take care of her emotional needs by visiting aLOT. It’s very healing for her and also for me.

    • Louise says:

      Chris, what an generous and lovely thing to do! Living on the East Coast, I know nothing about the West Coast, and would love to visit San Francisco with my husband and do some exploring. Or Seattle — another area I’ve heard so much about and want to visit. For a completely different climate choice, New Mexico!

      Thank you for all the work you put into your website, your blog entries, and the Summit – I am late to the Frequent Flyer bandwagon, and want to start catching up!

    • M. says:

      Oh, that’s mighty generous of you!
      I’d have to say I’d go visit my grandmotherβ€”she’s 100 this year, and doesn’t travel much anymore. Birmingham is about as close to her as I’d get (she’s in Mobile, AL) but that’s an awful lot closer than NYC where I live!

    • Pierre says:

      Almost 10 years ago, I left Corporate America & a company that grossed $96 million in 15 months. I left to to pursue my passion of making a life-changing difference in people’s lives. Most of my friends thought I was crazy since I had not been to six countries in my entire life at the time I set out to go to six my 1st year with absolutely NO MONEY!!! By the end of the year, I had been to South Africa, Nigeria, France, Trinidad/Tobago, China, & Spain. Since then, I have been to 5 of the continents. During the last 5 years however, I have only been away from home for 21 days. We recently had our 3rd child (13 days ago) and I am so ready to hit the road again. The tickets would used for a get away for my wife and I. I have been a stay-at-home dad the last 5 years.

      It’s important to note that I was connected to you thru one of my former kids (Leighton) that was apart of my youth ministry. He said, “Pierre, I finally met a guy that goes against the grain like you.” I recently performed the marriage ceremony of Leighton a month ago and one of the questions he asked me was, Are you still receiving Chris’ emails. I assured him I was I refuse to be normal…moving to S. Africa in December

    • Chris:

      You never cease to amaze me with your kindness and generosity.

      I’d fly Chicago to San Francisco because I’ve only been there once before on a mileage run so all I’ve seen is the airport.

    • Elizabeth Martin says:

      I called my Grandpa on my recent birthday. I was thankful that he was able to put a name to my voice, because each time I call it is a gamble. I told him we are separated by sixty years and two weeks, as I just turned thirty. He cheerfully proclaim in his altimeter’s-ridden state that he would wait for me to catch up. Unfortunately, life will keep turning while his memory fails him more each day. I would use these miles to visit my Grandpa, or Buppa as I call him, in Minnesota from my home base of Portland, Oregon. Thank you for your consideration.

    • Amy Baker says:

      I’d use one to go to San Francisco, a city that I’d love to explore. And the second would be for a trip back to Denver/Boulder, where I went to grad school and haven’t been in almost 10 years.

    • Vicki Simon says:

      I’ll take this opportunity to plug Southwest. I love Southwest. They are truly a basic, no-nonsense airline which I favor for many reasons, not the least of which is no baggage fees, and open seating. No-nonsense! Also, I can go back and forth to San Francisco regularly which I do for business. Oakland airport is beautiful and easy to navigate. (I love the sight of those papyrus bushes blowing in the wind on the edge of the runways). So, others have more compelling reasons to win the 50K miles, so I think they should go to one of them – a lucky one at that.

    • Marcela Musgrove says:

      Southwest is great! Flight attendants who tell jokes, snacks and free baggage.
      I’d use the miles to fly to El Paso, TX. My extended family lives across the border in Chihuahua,Mexico so from ELP can just take a short bus ride to see them for the holidays. It’s been several years since I’ve seen them so would be much appreciated!

    • Kaitlyn Baldwin says:

      If you ask me, my mom is a warrior. Despite a string of serious financial burdens and unexpected strains, she continues to be one of the most positive and uplifting people I know. In her mid-fifties, she works three jobs, including teaching middle school reading full time. Two of her kids have recently graduated (myself included, the oldest), one is off to the Marines, and her youngest (a wonderful surprise- born 14 years after the rest of the bunch) is 9-years-old and at home. My mom is constantly picking up tutoring jobs, training new teachers, whatever she can to stay on top of expenses and debts. She works around the clock and never takes time (or money) for herself. I live and work in NYC, at an education non-proft, which I love, but doesn’t equip me to give her everything I dream I can one day. With these 50,000 miles, I would be so grateful to fly my hardworking, loving mom to NYC, along with my 9-year-old sister. There is a direct route on SW from their home in Florida to my home here. I miss my baby sister and mom dearly and this would be an incredible holiday gift to us. I know my mom would love the vacation, and my sister would be awed by the holiday lights. Thank you!

    • Barrie Byron says:

      Thanks Chris!! Before my mom’s 78 birthday in April, I would travel Philadelphia to Nashville (PHL-BNA) and my mom would travel West Palm Beach to Nashville (PBI-BNA). We would use to time to walk down memory lane and build new memories. My cousins live in Nashville, and my mom hasn’t seen them since her sister passed away more than 5 years ago. Time flies… my family is dispersed around the globe… I’d love to be able to get my mom to see her nieces and nephews, and their kids… (I like the way you’re sharing… fabulous example for the rest of us!!)

    • anjali says:

      Sweeeettttt! Love miles! I would go from San francisco to New york… or New orleans.. so many choices! πŸ™‚

    • Ramai Gaasbeek says:

      Hi Chris,

      I would use the tickets to fly my wife and I to spend Christmas with her family in Vancouver and get a much needed change of scenery (from flat Florida) and a taste of travel that I haven’t experienced for a couple of years. Thank you for your generosity.


    • Sylvia Ashley says:

      I would travel with my 16-year-old daughter from Denver to either Boston or Providence, RI. She would love to tour Brown University, as well as several of the universities in the Boston area. We’d couchsurf in both Providence and Boston if possible to get a taste of both cities.

      Thanks, Chris, for the opportunity. Love your work!

    • Thu says:

      Thank you so much for offering the miles. I would love to get the miles so I could fly to New York since I have never been there before!

    • George says:

      I would visit a good friend of mine in the DC area I haven’t seen in 4 years.

    • Bridget Bleshenski says:

      Chris, so kind of you to offer your points like this! Everytime I fly with southwest, it’s been a wonderful experience. I would use the points to fly to South Carolina. I’ve never seen the east coast, and South Carolina has always been a dream of mine! Cheers!

    • Adam says:

      Keep up the awesomeness Chris! If I won the Rapid Reward miles I would fly to visit my father in Florida. He’d really appreciate a visit. I haven’t had the funds to be able to make a trip happen, so these points would be amazing to win.

    • Karin Goodwin says:

      I’d go to Phoenix, AZ, with my sister for the Phoenix Rock & Roll Marathon. Heck yeah! And then I’d have to actually train up…..

    • If the timing works out, I will use the tickets to take my wife to WDS next year! I was at WDS 2013 and it changed my life. Before I even left Portland I told her she had to go next year and bought us tickets. These mile would work perfectly for us since Branson, MO just opened up to southwest and has direct flights to PDX!

    • Susan says:

      It is so generous of you to give away these miles! My stepson’s wife recently left him – with a 6 year old and a 3 year old. To give my stepson some relief from divorce proceedings and single parenthood, I would use the miles to fly him and one of the kids (we’d have to pay for the other one!) from Milwaukee to the DC area to visit us at Christmas. It would be good for him to have something fun to look forward to and a change of scenery.

    • Amy says:

      I would fly from Chicago to San Diego to escape the cold winter for some sunshine at the beach.

    • Bob says:

      Hi Chris,
      Nice of you to offer these miles! They would be great for us since our daughter just got married and now lives in New Jersey and we live in Seattle. We plan on flying from Seattle to Newark several times this year to see her and the 50,000 SW miles would be a big help.

    • Two round trips from Tampa FL to Washington IAD to get on a plane to South Africa, and back. I would drive from South West Colorado, where I live off-the-grid, to Florida – pick up Kiley, one of my grand kids, and take her on a trip to South Africa, where we would see two of my children who live near Johannesburg.

    • TJ says:

      One for me and one for a friend who has never flown before. Here’s to one more person learning to love travel. Thanks!

    • peilan says:

      Where would I go? I would come up with a list of places I’d love to see and pick one w/ a random number generator. I would put a world map on the wall, close my eyes, and throw a dart and see where it lands. I would choose a breathtakingly beautiful place where a single human being can feel inspiration from the earth and her elements. In other words, I have no idea where I’d go. The circumference of the earth is ~ 25,000 miles. The width of the U.S. is about 3,000 miles. 50,000 miles = a set of wings to go explore!

    • Nora says:

      Hmmm, probably Cali, SF or LA. I got good friends in both of them, and they are about as far away as they can be in the continental US. OR PORTLAND where I’ve never been before. Something west coast for this east coaster!

    • Bonnie says:

      Hey from Alabama! Love your website! I would use the flights to go to a conference in Austin in February and to go see my best friend from childhood who lives in Phoenix! I love Southwest!

    • Eric says:

      Just found out about this site from my friends over at Nerd Fitness.

      As a single dad I would use the miles to visit family (with the kids), take the kids on one of the adventures that I have been promising (but have yet to afford), or give myself a holiday and visit one of the many countries on my bucket list (because I’m not dead yet!).

      Thanks Chris for the opportunity and for all crazy cool work that you are doing. Viva la revolucion!

    • Mike Callaghan says:

      Hi Chris, I’ve been following AONC for several years and love your unique and empowering advice.

      I’d choose to fly into Boston, from my home in Montana, and then head to Cape Cod & Nantucket. I grew up in New England and haven’t been back since leaving after graduting high school almost 30 years ago.

      There are so many relatives and places that I’d like to share with my wife.

      Keep up the great work!

    • Grant Taylor says:

      Chris, if I win the SWA points, then I’ll transfer them to AirTran so I can fly non-stop Austin to Cancun. Then, I’m on to Isla Mujeres and Merida.

    • Linda says:

      a new to me state! I have 32 to choose from.

    • Where will I go? The answer is really where WON’T I go. Fifty thousand miles would launch a grand “visit-all-my-old-friends-who-I-only-see-on-Facebook” tour. That’d be an amazing gift! Thanks for all you do.

    • Jill Conaway says:

      Wowsers, thank you Chris! This is could be serendipitous as I’ve been trying to find an affordable flight to fly from WI to Spokane WA. An animation project that we’ve been developing for 7 years is starting to get off the ground – literally! A 3-minute animated trailer of what will eventually be a pilot episode is going to be introduced at the Sandpoint Film Festival the weekend of Nov. 2nd. So we’re hoping to fly out Friday Nov. 1 to be there for the weekend. Do you see me jumping up and down? “Pick me! Pick me!” Cheers πŸ™‚

    • David says:

      Chris, my wife and I will celebrate 25 years of marriage in 2014. With two free tickets I would fly from Minneapolis to San Francisco or San Jose with my lovely wife in June. We would walk among the giant redwoods. Thank you.

    • Rex says:

      I’d use it to take my two girls to Ole Miss for a football weekend. They are high school sophomores so it would be great to spend the weekend with just me and the girls back where I went to school.

    • Martha says:

      Thanks for hosting! I’d love to fly to Los Angeles to visit friends that left New York.

    • Elle says:

      I would give them to my newly retired mother because I live in Hawaii, which is off the SW travel route, it looks like. But my mom has become an enthusiastic traveler, even on her budget, and I can barely keep track of where she is. She’d LOVE this! (So would I, if I could use it!)

    • Elise says:

      I’d like to go to either New Hampshire to visit good friends we don’t see often or San Diego to take the kids to LegoLand. Either way, it’d be nice to get away!

    • DeAnn says:

      I dream of becoming a world traveler someday – but for now I could use the points to fly to Dallas and visit my best friend who I have seen only once in the last 30 years.

    • Jason B says:

      I would fly to FLL or San Diego. I love beaches.

    • Erin O says:

      I would go somewhere beachy that was a nonstop from Denver so judging from the map that would be Cancun or Florida.

    • Judith Soffiantino says:

      I’d pick San Francisco. I traveled there many years ago and fell in LOVE with the city and haven’t made it back, but have always said I should.

      I’m also just excited that one of the people who post here will receive this amazing opportunity – really gracious gesture, Chris… thanks for that!

    • Lance says:

      Thanks for the heads up on SWA devaluing miles. Wasn’t aware!
      If I win the 2 tickets, I’m headed to Vegas. Cliche, but fun.

    • Hey Chris! I’m dating a beautiful girl in Nashville, Tennessee. Which is awesome. But I love in Portland, Oregon. I love all the miles/flights I can get for extra trips to see her.

    • Jamie says:

      Chris! Hey man, I actually JUST got the CC offer for the Southwest card from Chase yesterday. It looks like a great offer but I’m gonna mull it over until the weekend…who needs more plastic, anyway?

      Anyway, I regularly fly southwest from Oakland, CA in order to visit my childhood friends in San Diego and Seattle. One of our other friends, who I have been unable to visit cuz it’s NEVER the ‘Southwest $69 flight’ lives in Chicago. I’ve never been to the Windy City, but I KNOW my girl would LOVE it for us to take a trip out there and visit my buddy in med school.


      – Jamie

    • Sara says:

      I’d go visit my cousin and her family in California. I’ve only met her son once and he just had his second birthday. I’d love to hang out with the little guy some more!

    • Greg Lloyd says:

      Sweet November – With two free tickets, I’ll be off to Austin, Texas, for a late fall romp of music, hiking, and exploring this beautiful part of the country.

    • E.C. says:

      Hi Chris, Thanks for offering the 50,000 mile and contest.

      As a single father, I am excited to see my 6 year old daughter in person. She is coming from China and I will have her for next summer. I plan to take her to Los Angeles, to see Disneyland, other attractions, and relatives. This chance to win 50,000 miles can help me with the airfare cost, as she is coming with her grandma. Hence I pay for all of their travel (including international fare) /expense cost while in the US for two months.

    • Katrina says:

      I would visit my friends in Los Angeles again, and I would go visit my friend and his soon-to-be-fiancee in Alabama! πŸ™‚

    • Andrew H. says:

      My wife and I would go to Iowa to visit her family for the first time since we’ve been married as well as go to a good friends wedding.

    • Brianna says:

      I’d fly my parents out from Eugene to visit me where I am going to graduate school in Boston. They would stay in the little attic extra-bedroom of our apartment and I’d show them all around the city, campus, my building, and museums. Maybe even talk them into going rock climbing at the local gym!

    • Meghan says:

      I’d go to Seattle to eat and Ft. Lauderdale to visit the Florida Keys. Two vacations I’ve been wanting to take for so long!

    • Jonathan says:

      I would love take a honeymoon trip to Arizona and visit phoenix and head down to sedona. It’s a trip we’ve been talking about taking for sometime. We’ve down some international travel but not much domestic travel. I think we would have an absolute blast exploring that area.

    • Daniel says:

      Thank you Chris for this generous offer!!
      I would either fly to Ft. Lauderdale to catch my next cruise or finally show my wife Boston, since she always wanted to see it. Depends on when you would book the flight.

    • Great offer Chris. I love Southwest and have used your tips for travel hacking to get miles on Southwest already with great success. However, my wife and I have used all our miles up now πŸ™ which is a bummer because we were really hoping to come to Portland next July for the WDS as we are both launching new projects and were hoping to connect with like-minded community. So, if we were to
      win the miles you are generously giving away, it’s a no-brainer….Portland here we come!

    • Shawna says:

      I would fly to New Orleans! I really want to visit (not during Mardi Gras) and really try to immerse myself in the true Nola culture: music, food and good times.

    • emily says:

      I’d go to Portland to visit my friend and then have her visit me! Thanks πŸ™‚

    • Herman says:


      I would go from DC to Austin to visit my family, see the Longhorns play, and most of all the Formula One Grand Prix!!

    • Valerie Calabria says:

      I would either go to NYC or to Portland or Seattle, which are cities I’ve always wanted to see!

    • Thanks for gifting these miles, Chris. No frequent flier miles should *ever* go unredeemed!

      I know exactly where I’d go and Southwest is one of the only nonstop routes there from south Florida. I’d take my 16 yr.-old daughter with me on the FLL nonstop to PHX to see my brand new nephew scheduled to arrive in the world on or around November 7. My daughter would meet her new cousin and be able to tour a few colleges in the area, plus we could help out my brother and sister-in-law while they adjust to baby #2.

      Happy gifting!

    • Amanda says:

      Portland to explore on my own!

    • Gary Green says:

      Gotta go corner to corner with a typically generous deal like this – Lindbergh to La Guardia (SDC to NYC). Thanks Chris.

    • Valentina says:

      Hate playing the pity card but I had a really rough year so far after finding out about a health condition which completely shifted my reality and could really use a vacation…
      I would go to Hawaii or San Diego! Always wanted to try surfing!!!

    • Edgar Landa says:

      I am an adventure/endurance racer and getting around to cool places for awesome races is sometimes a challenge. I would use the tickets to travel to a city I have never been to before in which a Spartan Race or Goruck Challenge was being held! Both put on great events, are partnered with great charities and are run by great people who pay attention to the details.

    • Gaza says:

      Somewhere long the way re-gifting got a bad name. My mom. She complains. A lot. But she has a good heart. My family. Two sisters, one brother. Spread out: Virgina, Mississippi, Colorado, Oregon. My mom lives in the ‘family home’ in Portland – though none of us kids consider it the family home since it came a bit too late to win our affections as teenagers. “Our” home is a dumpy little 1,100 SF ranch built back before political correctness was invented. They’ve taken the sign down. I digress. Mom complains because she is lonely. My mom and dad were together 39 years. She really wanted to hit 40, but the cancer stole that from her too. That was 7 years ago. She hates Southwest. I’m sure they “were so rude” to her and her bag (kitchen sink included) is somehow always overweight. Checking in online is too complicated so she is forever in the “C” group. Middle seat. My mom is not a middle seat person. So should I “win”, I’d like to regift them to my mom.

      I’d like to send her to see my little brother (MSY). His 8y/o daughter doesn’t see enough of this side of the family. Nor does my brother really. Give her something new to complain about. “Its so humid!” Thanks.

    • Adam says:

      I’d use one ticket to fly to Boston to visit my best friend and one to fly to San Diego to visit my grandparents, whom I haven’t seen in a few years.

    • Rachel says:

      Home to New Hampshire, to meet my sister’s new baby (it’s my first time being an auntie and I can’t afford to make the trip).

    • June Eastman says:

      Southwest is one of my favorite airlines to travel because it flies from the airport closest to me and offers really good value on its frequent flyer miles. Two years ago, I opened a Southwest Rapid Reward Visa, that you pointed your readers too, and there was enough miles for three of us to take a round trip flight from New Hampshire to Colorado. I used other miles from other deals you recommended to rent a car and to book hotel rooms. We spent time traveling around Colorado, went up to Wyoming for a rodeo, and over to Utah to Moab, to visit some National parks in that area on my bucket list. We had a great vacation at a pretty low cost. I have pointed others to your website and at the Southwest card (which I use for many purchase). I can always use more miles from them!

    • Alex Demetriou says:


      First off, I’d rather just take advantage of the fact that you might be reading this comment. I love who you are and what you do. There’s that quote that you should either write things worth reading or do things worth writing. I think you’ve taken a similar stance with what I want to do with my life, and that’s both. Keep on rocking cause it’s people like you that keep me going.
      I’m a junior at the University of Michigan. I have huge dreams that I’m scared every teenager has until they “grow up” though I’ll probably be stubborn forever on making those dreams reality. I have no idea specifically where I’d go with those tickets but I think I have a general idea with what I’d want the trip to be like. I’d want to travel somewhere I know would be inspirational to me, which would probably be anywhere really different than what I’m used to. Yellowstone is the first thing that comes to mind, but seeing a famous comedian is also up there (one of my dreams is comedy). Visiting random friends in college would also be cool. Also I have a plan to backpack through America in a naive “Into the Wild” way, so plane tickets would make it a bit safer/lame.
      Thanks for reading!

    • denyse biagi says:

      Want to go to New Orleans.I haven’t seen my friend there since before Katrina

    • Glenyse says:

      My trusty nieces and nephews would be the lucky beneficiaries of those points. I’d send for all of them, to come play on the beach and have a great time with me in Florida.

    • Michael says:

      Thanks for the upbeat articles and info Chris. Tampa Bay is nice when the weather starts getting cooler. I think I would head there.

    • June Eastman says:

      I hit enter before I was done! I am saving miles for a graduation trip for my son and partner to Seattle, where we will cruise up to Alaska. Those points will cover the tickets to Seattle πŸ™‚

    • Robin says:

      I live in cold Washington State and my lifelong friend lives in damp Massachusetts and we were just plotting to get together in Phoenix so we can rent a car, go see the wild places and touch a saguaro. You know you want to be part of that.

      PS thanks for all, all, ALL you do.

    • Terry says:

      I’d visit my cousins in Chicago. It’s been a rough year with my last surviving parent dying and both of theirs. Being together could only help.

      Loved your book

    • Lovin’ your newsletters, thanks for the inspiration to take to the friendly skies frequently. I applied and received the Hilton Credit card after reading one of your posts and it’s already paying off. THANKS for being a leader in the Live the Life you Want to arena. My family and I are looking forward to the summit next summer and we’re inviting a few friends.



    • Kelly Lira says:

      SF! Spontaneous weekend wine country visit. Yes. Please.

    • Veronica Holtz says:

      I would go home for the holidays! We’re moving halfway across the country from the region where our families live. So I’d either go BOS->MSY for Thanksgiving or BOS->ICT for xmas! πŸ™‚

    • Darn these contacts!!! That was supposed to be a smiley face in the comment above not a sad face, AGHHHHH. Trying again……..


      OK got it right this time.

    • Sarah says:

      I’d take my son (6 years old) to a comic book convention!

    • With those Southwest miles, my wife, baby girl, and I will fly to New York. From there, we’ll take a different flight to Paris. We plan to live there for a month and learn French because I can work remotely. I have family in Lyon who haven’t met Salem, so we’d be able to spend time with them. I’d probably hit up some of my travel writer friends and figure out how to get the whole trip paid for by someone who would be interested in hiring a writer to talk about traveling and living abroad with a young child.

      So that’s the plan! Thanks for the opportunity to win the miles, Chris.

    • tiffany l says:

      i would go to atlanta and nashville. i think. there are so many options!

    • Kat says:

      My mom and I haven’t seen each other in a year, so we’re planning a trip to Austin. We’re going to be massive dorks and enjoy some (read: lots of) TexMex followed by a music tour on electric bikes. We just need to pick the dates and get some tix! (Not to sway your feline assistant, but I rather adore my namesake and may or may not travel with cans of tuna.)

    • Susan Stein says:

      Chris, you are the awesomest person I kinda know! It’s way cool you are giving away miles. I live 15 minutes away from Love Field in Dallas, Southwest’s hub, so I fly Southwest almost exclusively. I love to travel, so in a few years, after my credit recovers from my newly ex-husband’s chronic overspending, I will be travel hacking my way all over the place. Don’t feel bad for me, it was a life lesson learned.

      First I will use your miles to book my ticket to WDS2014. Last year was my first one and this introvert was blown away. I drove up to Portland from here and spent 3 weeks afterwards road tripping through Washington, Montana, South Dakota and Colorado. An incredible experience all the way around. As much I enjoy road tripping, it’s unlikely I will have that luxury next summer, so I will be flying to WDS2014.

      I will use the other ticket to spend this Thanksgiving in Philadelphia with my daughter. There is nothing I am more thankful for than my amazing daughter, who, at just 20 years of age, is already rockin’ the world with her own inspiring vision.

      Thanks for considering, Chris.

    • Bunny says:

      I would go to Chicago to visit my husband’s aunt! And to visit their many wonderful restaurants.

    • Wow, great idea! You sure have a lot of them (…and yes, I realize that with the draw, flattery will get me nowhere – BUT the tickets certainly would get me and the hubby somewhere). As for where? Anywhere is good. It’s all good!

    • Greg says:

      My wife purchased her wedding dress in her hometown and was automatically entered into a San Diego honeymoon getaway package. After we were married and settled in 400 miles away from her hometown, we found out she was the winner! Unfortunately, between work and school we weren’t able to make it back in person to redeem the trip to San Diego. Our 5th anniversary is coming up this year, and I would totally surprise her with the missed trip!

    • Jody says:

      I would use the miles to fly my family from Seattle to St. Louis to visit family. My kids rarely see their grandparents or cousins. It is not a glamorous trip, but one important to our family.

    • Ailish says:

      My boyfriend and I are considering starting a food truck using produce from his farm, and I’d really like to take him to Portland, OR, to do some field research. I was really impressed by the food cart pods when I visited there last December!

      Thanks for running this contest, and thanks for the informative and thought-provoking newsletters. I haven’t commented before, but I really enjoy them!

    • Martice says:

      Wow! Thank you for such an awesome give away! I can’t even begin with where I would go. From the beaches of the Caribbean to the hot springs of Colorado!

      I’m a recent grad that has been searching for my purpose in life. I thought I found it once I founded my org girlsgoingglobal to expose inner city girls to world culture but after a year I feel burned out! I know I need a trip away to renew my spirit to help these girls know that it’s not about where you come from but where you go in life!

    • John says:

      To pick a spot on the map and have an adventure!!! Yes

    • Jared says:

      Thanks for all your posts Chris! I’d use the miles to go with my girlfriend to New York (I’ve never been!) so she can show me all the off-the-beaten-path spots she loves so much about the city.

    • Jennifer says:

      My boyfriend and I have long dreamed of traveling across the country. With the miles, we would fly to San Diego, then take a couple weeks to drive home to Buffalo.

    • Willena says:

      I would like to win these miles because I want to go to Milwaukee. Although you, Chris, have been to all the countries in the world, I am close to achieving my goal of making it to all the states in the U.S. I am 3 away…. Alaska, Hawaii, and Wisconsin. Now, how I’ve missed Wisconsin in all my traveling, I’m not really sure, but this would be the perfect opportunity to fill in the gap!

    • Barb Varian says:

      I would take my 8th grade daughter who is home schooling to Washington D.C. because she is studying US History and what better place to learn it!

    • Tonya says:

      Hi Chris,
      I would love to win these points!! I have a passion for travel, but as a social worker, my budget does not always match my travel ambitions. I’m also starting to use some of your travel hacks. These points would help a girl out tremendously πŸ™‚ I’d probably use them on my quest to explore Yosemite, the Sierras, and Big Sur.

    • Greg M. says:

      Southwest is my bread-and-butter airline as a Dallas native and frequent regional traveler. I’ve watched them shift away from a number-of-flights-based rewards program (those were the days!) to the Rapid Rewards model and stayed loyal as their regional prices almost always can’t be beat.

      I’d use the 50,000 miles to take a trip with my younger sister – to Washington D.C. this December. Neither of us has visited before. I’ve wanted to explore the historical aspect of the city and its monuments for many years, and it still seems unsettling to the novice traveler in me that I haven’t visited our nation’s capital. The entire family had a vacation planned to DC as the “summer family trip” for June 2012… and the tightened security after 9/11 made it impossible to do the city (or the trip) justice at the time. Top on the domestic bucket list.

    • Ann says:

      Hi, Chris. I’d use the ticket to go to the Women 2.0 Conference in Las Vegas in November. I scraped the money together for the conference fee with a hope that airfares would drop (yes, I’m a dreamer). I make a great red velvet cake. Would that…*sway* your decision, at all?

    • Not me. I’m swimming in miles like you, and I use them to fly friends to hang with me or vice-versa.

      My friend Regina lost her husband suddenly two years ago, then found out she had terminal brain cancer, and is in hospice care now. Her daughter Kathryn needs them to fly back and forth from Memphis to Detroit to be with her.

      That’s my vote. Meow?

      Randall in Maine

    • SHawn says:

      In the spirit of non-conformity, I’d max the adventure on this: bus ride from Buffalo to Key West (amazing free spirits and ‘One Human Family’). SOUTHWEST from KEY WEST to VEGAS (I’ve always wanted to write, and I’m doing it: a screenplay in which my lead character’s sister lives in Vegas burbs, so I gotta see Vegas for research πŸ™‚ Then, OPEN JAW time, I’d grab a bus Vegas to Albuquerque via the amazing Coyote Buttes between Utah and Arizona – they look too cool to miss in this life – and FLIGHT TWO would be ALBUQUERQUE to NYC (no one needs a reason to visit NY but I’d like to see some plays.) And then bus ride back to Ottawa, Canada. Too much explanation? Sorry.

    • Chris says:

      This is epic, Chris. I would send my parents to any city they choose to have time together: away from jobs, away from realities, away from the struggles of living 24 hours apart amidst their larger “final home” migration goal. They deserve to travel; something they never make time for themselves. C’est la vie!

    • Roxanne says:

      My beautiful, young sister (under 50) has breast cancer. Thank God she had a mammogram scheduled which found the lump even after a perfectly good mammogram last year. She’s had surgery already and undergoing chemo as we speak. My mom wants to take my sister on a trip to from Boston to Las Vegas for something fun to do (for a change!), esp after her chemo treatments end in January. Mom has a few nights stay already covered, but she wasn’t sure if she could manage the cost of the flights. It would mean a lot to both of them and me, of course. Thanks Chris and Mr. Kitty Assistant.

    • Laura says:

      Thanks for making these miles available, Chris! I love flying Southwest and have been known to drive the 3 miles to Nashville to take a flight on Southwest. I’d have to say Portland or Seattle would be my destination of choice so that I could do the WDS!

    • Laura says:

      That was actually 3 hours, not 3 miles to Nashville… πŸ˜‰

    • Well, I see Portland and Austin both on their route, so I’d be flying to World Domination Summit in July 2014! Tickets bought? Check. On iCal? Check. Ready to crush in the natural health care for animals niche? Check!

      See you there, whether you fly me or not, Chris!

      Thanks for the shot.

    • Brandon says:

      A bit of a round about way to do this, but I want to try to travel to Tanzania to visit a friend during the first half of next year, so I would use the miles to position myself at a better airport to fly out of from the US. (Speaking of which, do you have suggestions for least expensive airports in the US to fly to Tanzania from?) The second ticket would be to bring another friend!

      Keep up the great posts!

    • Carolina says:

      Hi Chris, this is awesome. I would either go to Charleston, South Carolina to begin my U.S.A. travels (quite sparse compared to the rest of the world). Or I would go to Oklahoma City to visit our fellow community member, Global Table Adventures. Or, I would go to San Francisco to visit Angela :D. I would either go with my mom or my husband (preferably my mom as she hasn’t gotten to travel much). I took her to Morocco and Ukraine and she had a total total blast.

    • Michelle says:

      Thanks, Chris! You are one of the most super-swell people I know. Truly.

      I fly SWA! But their prices have skyrocketed lately. Yikes!

      I would really like to go to visit my 92 year-old grandmother in Fort Meyers, Florida. She’s been asking me to come for a visit as of late. After a recent heart attack, she told my mother that she feels “different”, she’s made peace with death and she’s ready to join my grandfather.

      Now, the woman is the human version of the Energizer Bunny. She survived a nearly fatal car accident — twice! — and a heart attack at 92, but . . . she is “up there” in age and a bit uncharacteristically morbid at the moment.

      Traveling from Phoenix, a trip to Florida is a pricey SWA ticket. Nana and I would be ever-so-appreciative of a freebie! I hope that she feels up to taking me to her Zumba class!

      If I had the good fortune of winning a 2nd ticket, I would travel to a city that I’ve never been to and sit and stay awhile. I recently unearthed freedom in my life when I finally said goodbye to The Man and quit my corporate career to follow my bliss. Granted, I’m not making any money — yet! — but I am rich in time! And I have a yearning to explore . . .

    • Vivian says:

      Simply, love! Very generous of you to share. πŸ™‚

      To New York to see my son @West Point from the great state of Texas <3

    • Ryan McRae says:

      Hey Chris. I’d use the tickets to give to troops I worked with in Afghanistan and anything left I would see charity:water in New York. And on the way, I’d write you 20 haikus.

      Those free points would mean
      Soldiers get to fly for free.
      Thanks, Chris Guillebeau!

    • Gabe says:

      Thanks Chris for this awesome opportunity. I would use the miles to get a ticket to Louisiana in November for a good friends wedding and to take a trip out to Portland in the Spring with a group of friends to get out of Vegas for a while and see something other than concrete and bright lights.

    • Kelly says:

      Wow, lots of comments already.

      My daughter is attending University of North Texas, just outside of Dallas. My other daughter is attending Texas Women’s College in the same town. (They room together.)

      If I were to win the miles, I’d have you book send my two girls home for Christmas.


    • Chris, you are always so gracious in your offerings. There needs to be more people in the world with your giving nature.

      I as a few people said above, am nowhere deserving as some of the stories above. At first I was going to say I would go to Portland for the World Domination Summit. If chosen, I think I could have afforded the ticket for the next set of sales with some tax refund money.

      I’ve only flown once and that was with my wife to Jamaica for our honeymoon. Unfortunately, we didn’t really pick the best time to go because she was pregnant and sick in the hotel room the entire time. I’d take her to Portland anyway because of how beautiful I hear the city is.

      Thanks again for this awesome offer man. Even if I don’t get picked, I always enjoy the anticipation of having a chance.


    • Christina says:

      Whoa, so generous of you! With winter coming up and some serious changes in my personal life [read: single now :)], I think I’d put all the warm stops in a hat and draw– anything to temporarily escape the winter doldrums of the Northeast!

    • Mike Vardy says:


      It’s great that (once again) you’re being so generous…

      If I were to win the points, I’d take my wife to somewhere hot and has a beach she could get the much-deserved R&R that she needs. For the past several years while I’ve been building Productivityist, she’s been in my corner doing all she can on the home front to keep things running smoothly. She is my biggest supporter and she’s overdue for a vacation. These points would go a long way in making that happen.

      Thanks again — and see you at WDS 2014!

    • Christina says:

      I would use the tickets to take my husband to Seattle. He is a disabled veteran who recently got out of the military and who has had a lot of trouble finding a job. He is also an aviation buff and has always wanted to take a tour of the Boeing factory that is up there!! He would really love that for his 31st birthday.

    • Donnie Law says:

      Chris I’m glad to see some book recommendations. As someone who LOVED the $100 startup I would love to know more about what you’re reading.

    • Suzanne Schmidt says:

      Would Love and appreciate the points! I live near PDX and need to get my son who is a Senior this year to Tampa Bay to visit a few colleges he is interested in attending. As a single mom, this visit is a challenge, and we’d both appreciate it. Thanks for the possible opportunity.

    • Lisa says:

      Hi Chris! Recently, my husband relocated a sister he had lost track of more than 30 years ago. I met her for the first time in Phoenix last year and we clicked immediately. She would love to visit St. Louis and see her long-lost grandmother (possibly for the last time) but with three daughters, the cost is prohibitive. I would use the tickets to help bring her and her family home for a visit!

    • Max H says:

      My wife and I are trying to swing a trip to see Asheville, NC before she is too pregnant to fly–call it a baby moon I guess–but can’t seem to make the finances work. We would use these miles to fly to Raleigh-Durham and then make the beautiful drive across NC to Asheville . . . And she could use the time to read $100 Startup, to ponder her new career post-baby!

    • Alicia says:

      After finishing up four months volunteering in Peru on a local bird project, I’ll be flying back to the States thirsty to continue the adventure. A fellow vagabond is giving a go at hard work on a fishing boat in the Florida Keys, so why not take my wings out for another stretch and change my name from “bird lady” to “fish lady”?

    • Eva says:

      Most definitely San Francisco! Visited for the first time a couple months back and I can’t wait to go back, incredibly amazing city.

      Thank you Chris for all that you do!

    • Kayla story says:

      Thanks for the heads up about the southwest devaluation, had no idea. If I won two tickets I’d go to Puerto Rico this winter. There is an annual bike polo tournament there to beat the cold and I’d like to take myself and my partner! Thanks.

    • Marian says:

      I would use the miles to get my boyfriend out of the country for the very first time!

    • frans schuman says:

      Thanks for this opportunity Chris. I would use the tickets to book a connecting flight from New York to San Diego, coming from Paris. I’m a singer songwriter and I’d like to tour the west coast…

    • Jen says:

      My boyfriend and I are trying to get to Orlando soon. He really wants to see the Simpsons expansion at Universal Studios and I have yet to see the World of Harry Potter. Can’t wait to get there and enjoy a mug o’ butterbeer. Whoo-hoo!
      ~Sincerely, Jen and her kid-at-heart boyfriend

    • Michael Melloy says:

      Chris, inspired by your story and $100 Startup, am finishing plans to travel, do, eat, write and photograph, beginning in Ecuador and Peru in October. But the 50,000 miles would go towards a trip to Myanmar, from there . . .

      Just registered the URL for, will be launching in October.

    • Wendy says:

      Send me from Love Field to Seattle for the December 2 Monday Night Football game! My New Orleans Saints will be a long way from home and they will need fans at the game!!!

    • Peter L says:

      I’d use the tickets to visit family in LA!

    • Bryan says:

      Hi Chris,

      I’ve been suffering from a chronic injury for the last 6-7 months, and haven’t been able to travel much. I’m finally feeling better, and I’d love to use the miles to travel across the country to NY to be with my folks for Thanksgiving.

      Thanks, and keep up the great work!


    • I luv Southwest Airlines because they’ve always under promised and over delivered and they do it with true hospitality. I recently read in their on flight magazine Spirit that their acceptance rate of applicants is much, much lower than that of any ivy league school! Having flown economy on most of the major airlines and been valued by what I paid for their ticket, Southwest is now my preferred airline. If I had a spare 50,000 miles, I’d treat my husband and I to a Puerto Rico getaway! Thanks for your generosity.

    • Angie T says:

      Thanks, Chris! I would fly to Nashville or Charleston to see my mom!

    • Christy says:

      I plan to travel abroad long term next year (and hopefully use some of my new travel hacking points to get there!), so I would use Southwest points to visit my family for the holidays this winter.

    • andrea says:

      Hi Chris, would love to win these points (like everyone else πŸ™‚ I returned from living overseas 9 months ago because my mom is sick and I miss it and miss my friends…so would love to go back or go somewhere new…so many great place to see and people to meet.

    • Rachel says:

      I’d fly to San Francisco, to catch up with old friends and enjoy their mild winter weather. My budget doesn’t make a get together like this easy.

    • Tom Meitner says:

      Thanks for doing this, Chris – you’re the man! I would love to take my wife to Washington DC, so I’d fly to DCA so that I could show her our nation’s capital (she’s never been)! Thanks again!

    • Jenny says:

      I would have to take my boyfriend to the beach. We’ve been together almost 6 years and have yet to go to florida together. Gulf side where I know the sand is white πŸ™‚

    • Chris says:

      From one Chris to another, I would happily use the miles on Southwest to travel to San Francisco to experience the foods and sights of the area. Thanks for sharing your adventures on traveling throughout the world!

    • Christina says:

      Portland, Oregon! Just got back after falling head over heels with the town! Want to make it back as soon as possible to see if this born and raised East Coast girl has what it takes do take the giant leap and move to this amazing place full of wonderful, unique, and friendly people!

    • Seshu says:

      Chris – I fly Southwest when I can mostly because of their luggage policy. As a photographer, I end carrying extra equipment and it’s almost never an issue and no extra charge on the flights. I also like Southwest because it flies to Albuquerque. I would use the miles to go out to the Santa Fe Photo Workshops to learn from a master photographer or two. Hook me up will ya?

    • Kristen says:

      Thanks for sharing the wealth, Chris! My fiance and I are trying to run a race in all 50 states. We fly Southwest whenever we can, and would use these points to get to some of the harder to reach locations on our list: The Dakotas, Maine, Washington. As you’ve said before, running is a great way to get to know a city!

    • Susan says:

      Awesome offer, Chris!

      I would use the miles to realize an “unconventional life” dream I have had for a long time. The dream is to write a non-fiction book: a true, chilling but inspirational story about a tragedy in which 13 boy scouts/leaders died on a high adventure wilderness trip in So Utah.

      Writing this book requires me to travel for research and interviews. I began the research/writing process a year ago. Big surprise for me: interviewing survivors was not just getting info, it was an enormous gift for people whose stories need to be told and heard.

      I would use your generosity to fly from Chicago where I live, with a good friend in Virginia who is collaborating with me on this book using her skills as a genealogist & researcher to help me locate survivors, rare photos, etc. We would fly into Salt Lake City, drive to So Utah and stick around for a several weeks, interviewing everyone we can, digging through archives and beginning to craft a manuscript for the book.

      If we are lucky enough to use your miles, I promise to provide photos and updates from our adventures tracking the story where it happened … in wilderness places and small towns.

    • Christina recaΓ±o says:

      Hi Chris!

      I had to jump on this offer as soon as I read the newsletter! If I were to win I’d use the two free tickets to take my mother back to her old stomping grounds in New England. This year marks thirty years since her graduation from Simons Rock College in MA. I just know that she would love to go back for the reunion this year and have me there with her. Also, I would love to explore New England during the Fall/Winter season.

    • Gretchen L says:

      I just came back from a road trip to Asheville from Iowa with a good friend who generously footed the bill. I would love to pay her back, especially with air miles because she really doesn’t like being in the car that much and yet she’s ridden in a car for thousands of miles with me. Her in-laws are in Las Vegas, so maybe she (and her husband?) could use them for that, although unfortunately it’s at least a 4 hour drive to any airport that flies Southwest. It would probably cost the same to fly to the nearest airport as to just fly to Vegas Maybe I could drive them. Or maybe she would pick somewhere else to go. Or something. At any rate, I thought it would be worth trying. Thank you!

    • Bryn says:

      I love southwest and only wish they flew more internationally! I sing their praises all the time and my husband just rolls his eyes (As he’s relegated to the B boarding area no less). I’d use the points to head to New York with the madre – she’s never been. I’m pretty savvy with my points, so I’m hoping to have a few leftover to make the (shorter) jaunt to Portland for WDS 2014!

    • kathy says:

      I am from the northeast. Have never been out west. Always wanted to, just never allowed myself to spend that much money for pure enjoyment. If I would win the tickets, I would give my husband the other ticket and take off for a Grand Canyon, Las Vegas, Yosimite, and Los Angeles loop. It would be a trip of a lifetime for a couple of homebodies.

    • Sean Rogers says:

      I’d use the miles to go to this next WDS! I missed out on the last one due to a combo of timing and not being in the budget at all (after a lot of other travel). With the travel side sorted I’d have no excuse not to get there this time. πŸ˜‰

    • Mitch says:

      I’d use the tickets to fly down to Austin for a few days. I keep hearing good things about that place.

      Thanks for all your work, Chris, I don’t usually comment on anything, but I read your blog regularly and your book, The $100 Startup, has inspired me to make my own microbusiness. Keep up the good work!

    • Rachel says:

      I’d take my wonderful, but very poor and pregnant best friend somewhere away from the cold, grey winter in Utah. Perhaps Florida! Ohhhhh. Now I’m dreaming.

    • A couple of years ago, one of my nephews said he wanted to go on a plane. I told him I’d be happy to take him, which started a project of sorts to get all four of my sister’s children on a plane. I’ve succeeded in traveling with three of them (our destinations were Seattle, Paris, and San Francisco) and now I’m left with the fourth kiddo, the one that got me thinking about it in the first place. I’d take him wherever he wanted to go (obviously within SW’s network), as long as he hadn’t already been there. πŸ™‚

    • Linda says:

      Wow, being able to travel would be a dream come true!

    • Nina P says:

      Somewhere new for no other reason than I’ve never been there. How fun! Just to choose anywhere and go.

    • chris says:

      I had just pre-ordered Die Empty, and committed to attending WDS 2014, without knowing how I am going to get there…

    • Gemma Utting says:

      Gosh thanks!
      I’d use this to bring our family together for Christmas! My husband and I have been working for 2 years in New Zealand (hey you gotta go where the jobs are – right) but we’ve SO missed our son – who needed to stay in the USA to finish college. We are moving back to Boise, Idaho with no jobs – just a longing for “home”. So – miles to fly Charlie out to Boise for Christmas, and then one more trip so we can go see him in Portland in Spring: heaven!!

    • Steve says:

      Nashville… cause I’ve traveled the world and barely seen my own U-S of A

    • I hope I win … there are a few great Southwest trips I hope to make in the next year to meet up with entrepreneurs, hopefully even in Portland.

    • Jim Krenz says:

      I would use one ticket to visit my dad, in Davis Junction, IL. He is 87 now, and I haven’t seen him in several years.

      I would use the other ticket to go to Las Vegas, to see Penn & Teller, the Blue Man Group and other magical shows.

    • Colt Melrose says:

      I would take my wife on a vacation before we adopt our first son. Probably somewhere in the Northeast since the leaves are about to start changing.

    • Joey says:

      Hi Chris,

      Wow, what a great way to spend your miles! Thanks for the opportunity! πŸ™‚

      Having just returned to the East Coast from Portland, OR a few weeks ago, I am already itching to get myself back to the Pacific Northwest. This time around I think I’d like to make my way to Seattle, a place I’ve always wanted to visit but have never gotten around to exploring.

      Thanks again, Chris! And congratulations in advance to the winner!

    • Chris says:

      I like flying Southwest. If I was chosen I would fly to Charleston to visit my friend Louie who I haven’t seen in 11 years. My husband, Louie, and I were the 3 musketeers. My husband passed away 7 years ago, I’d love to see Lou and feel the old time comfort.

    • I would use the miles to take my sweetheart on a sun trip in Southern CA – flying into Ontario. We’d go visit a friend of ours who’s an amazing painter, finally get a private guided tour of the Getty with another friend, and have a break from the Portland Winter. We’ve only had two vacations together in seven years, so the chance to do this kind of getaway would be that much sweeter.

    • Brian says:

      Thanks for the opportunity and your generosity. I would use the miles to fly out to my cousin’s wedding in Charleston, where I’ve never been. I’ve made it a goal to visit at least 3 new places a year.

    • Henna says:

      I am recent college grad so this summer I covered all the West Coast on my 5,000 mile roadtrip to WDS. I would love to take my mom somewhere and kick off my plan to cover the East! We always talked about New York or Orlando so that would be nice start.

    • Kristin Jackman says:

      It’s so inspiring to be part of your tribe. Its exciting to read the comments and imagine the great experiences everyone will have tickets or no tickets. I don’t think you can make a bad choice! We’re all committed to making our lives about the experiences, especially those that come with travel. I’m a photographer working my way out of a desk job, inspired by my Iraq-vet turned acting student boyfriend. For us, it’s about meeting people along the way and working them into our art. We’d probably fly from DCA to Boise and rent a car and road trip to Seattle or Portland. Or maybe Albuquerque to San Diego. Taking pictures and writing screenplays along the way.

      Good luck!

    • Jan S says:

      Thank you Chris for your thoughtful and generous spirit! I attended WDS for the first time this year and was so moved by it. If I was the recipient of free air miles I would use them to travel to North Carolina to visit my cousins I’ve never met. In return, I would pledge to use that trip to talk up Charity Water and solicit donations for the organization with a goal of $7,500 within 60 days of returning back home. I am an introvert and sadly, I barely talked to anyone at WDS. I am working hard to change that about myself and not be afraid or insecure to talk to people. Having the challenging goal of raising $7,500 for Charity Water would push me out of my shell and possibly change my life. Thank you Chris for all you do!

    • Kat says:

      Well, this isn’t very exciting, but I haven’t been able to see my parents in forever, and I miss my mom and dad terribly. They’re down in Texas (Dallas Love Field) and I’m up in Baltimore. With the tickets I could get down there for Thanksgiving AND afford to bring my dog Henri with me — Southwest charges 75 or 100 each way for pets, which on top of the airfare just makes it impossible to do.

      Like I said, hardly a glamorous trip, but even thirty-somethings miss their moms.

    • Tom Tiernan says:

      I’d visit places so bold
      I’ll never want to grow old
      On Southwest I’ll go
      To California and maybe even Ohio
      I can’t wait to see all the places I”ll be
      So, please take a chance on me

      Thanks, Chris. You’re a generous spirit

    • Margaret says:

      I’ve never had much opportunity to travel but the desire to see the world has really started to gnaw at me. I had kids quite young and it seems many things, travel included, were put on the back burner while I focused on raising a family. My beautiful daughters are lovely but it would be wonderful if my spouse and I could travel somewhere, just the two of us, for the hell of it!
      I’d choose Las Vegas or Austin or maybe San Francisco or New York!
      The trip would be a catalyst to bigger and better things I’m sure!

    • Noah Willman says:

      I would go to montreal

    • Marq Romero says:

      First of all thanks for giving us the opportunity to score 50,000 miles!!! Insane!!
      My wife and I are looking to attend our friends wedding in Miami in February so 50,000 miles would help so much!! Thank you again!!

    • Zach Devine says:

      I would use the tickets to visit Portland and visit my family!!

    • jess says:

      A trip to New York would be awesome! Thanks!

    • Suzanne says:

      ME + 50,000miles = Exciting new adventures

    • Wes Luke says:

      Chris, Read your book in 2010 when I was living in Hawaii working with Surfing the Nations, Humanitarian Organization. I always believed I was created to create beauty with the life I was given so I didn’t want my life to be controlled by the lies of culture or have someone put me in a box. After reading your book “The Art of Non-Comformity” I entered on a journey, 8 month skate tour to 12 countries around the world all funded through events I did using my gift in skateboarding to give back to others, teaching skate camps, helping assisting in skatepark builds, and even teaching surf. In the last two years been blessed to travel the world to 15 countries, been on tv sharing my story in Egypt which went out to about a million viewers and recently returned from Switzerland from judging a skate contest and had two tv interviews and two magazine interviews. Dreams really do come true but I learned you have to fight for them and be willing to minimize possessions and sacrifice and work hard to keep dreams a reality. From one artist to another, thanks for being faithful in living your dream-creating something that adds value to the lives of others like myself. Hope we meet somday. Cheers

    • Jacob Machado says:

      I am a recent college grad. I have been flying southwest since I started school a little over 4 years ago and have been able to rack up a fair number of Southwest points that I have been able to use for flights to weddings, or travel between school and home. Since graduation my close friends have scattered thorughout the US with their new jobs. I am in Colorado and I would use the flights to fly myself from Colorado and a friend from somehwere else to either Florida or California to spend a week with friends in those areas and escape the winter cold.

    • Jess says:

      What a generous offer! I would travel to Houston. Why Houston? I want take an artist pilgrimage to visit the Rothko Chapel and see the Menil’s collection of Cy Twombly pieces. I’ve been wanting to do this for a long time and haven’t been able to.

    • Wes Luke says:

      If I had two free tickets…Currently Im moving to NYC. I would fly from NYC and invite my friend I grew up skateboarding with who resides in South Carolina, to fly to LA to visit a friend in Hollywood who recently played Jay Moriarty in the movie “Chasing Mavericks” and meet up to reunite and have a week of hitting up skateparks in LA area.

    • Barbara says:

      What a generous gesture! My husband and I almost never get to travel. I’m expecting my first grandchild next May, who will be born clear across the country. Being able to visit with family is very high on my wish list, and I would dearly love to fly from Portland to be there when the new baby is born in northern Virginia. Also, hubby has never been to D.C., but I used to live there back in the 70s — my daughter now lives near where I used to live. I would love to introduce my husband to D.C. and go museum hopping! A trip like this would be SUCH a blessing.

    • Shannon says:

      What an amazing opportunity! I am currently a student with little funds for travel so a trip to visit my good friend in Seattle is how I would use the ticket.

    • Staci B. says:

      I would love to use those Southwest points to fly from Phoenix to Portland, OR. My daughter is a high school senior and she is looking at colleges to apply to right now (wants to be a veterinarian) and loves Oregon. Our whole family is planning to re-locate with her as we all love the area, so we would like to fly up together and check out the colleges and housing for her, and also the housing and job opportunities (travel industry) for the rest of our family! We would love to take you out for dinner while there if you are available…

    • Thanks so much for the contes Chris. My wife and I would fly to Breckenridge, CO to ski and snowboard this winter. We made our first trip out west in August and absolutely fell in love with Colorado. Such a beautiful state!

      Thanks for everything you do!

    • Erin S. says:

      I would go to San Diego with my fiancΓ© to one of my best friend’s weddings πŸ™‚

    • John Albers says:


      I’d take my bride (& mother if 4) on the 22d anniversary trip we missed and celebrate my upcoming retirement from the Marine Corps.

      Thanks for the chance at the miles. Semper Fi

    • Gregg says:

      I would travel to Tucson to do some birding, especially all of the hummingbirds that area is famous for!

    • Dave says:

      With the miles I would give my mom a roundtrip ticket from California to Minnesota to visit her parents before they move from their home to a senior community this winter.

    • andrea perez says:

      If I won I would very much like to visit my kids in Denver Colorado via Norfolk Virginia. I miss my grandbaby,(and the kids too of course) So nice of you to share!

    • Mikell Sloan says:

      Many thanks for the giveaway! I would use the miles to book a trip to Puerto Rico to escape the snowy Denver winter for a spell.

    • Shawna says:

      I’d fly to Neverland. The fairies have said Captain Hook has jacked up the rates to 50,000 points now… :/

      In all seriousness, the husband and I would most likely fly out to Seattle or Portland. We’re looking to move out of Ohio within the next year and would like to explore a couple new cities before making a decision. The northwest coast is on our list of places to call home unless, of course, Neverland becomes an option on that ol’ route map. πŸ˜‰

      To Chris, biased judges and the feline assistant: Thank you for your consideration!

    • Greg says:

      I would literally throw a dart at the US map, and whatever major city it lands closest to, then I’ll fly there. Or else, if you choose me, I will let your readers decide which random city I should fly to. Then I’ll proceed to have the greatest long weekend of my life.

    • Brian says:

      I think I would fly to Boston… or San Juan.

    • Kate says:

      I’d use the ticket to go from Panama City Beach (where my husband is stationed) to Pittsburgh to see my friends get married. She’s American, he’s Italian, and they’ve been scrimping and saving to get enough money to get married in the US. We want to help them cover a few wedding costs, but we’re all graduate students and none of us are really rolling in the dough right now either. Getting a free plane ticket would help me direct my meager funds to help them have a special day.

    • Cole Matson says:

      Starting from my parents’ home in Norfolk, VA, I’d fly to Denver to drive to western Kansas to see my mother’s family for Christmas. Then I’d fly to Seattle/Tacoma to be able to attend a theatre conference in Vancouver which I’m helping to plan, assuming the timing works out. Then I would fly to New York to speak to several people about starting a residential Catholic artists’ community offering low-cost housing to actors new to the city (irrespective of faith commitment), and then would finally return home to Norfolk (before flying back to the UK, where I live, using my own money – not quite enough miles yet for that ticket). I can handle flying home for Christmas, but don’t think I’m able to afford the career-boosting trips to Vancouver and New York as well, at the moment. I’m finishing my PhD, so am trying to lay the groundwork for next year, and a mission to provide pastoral care to artists is part of it.

      Thanks for the opportunity, Chris!

    • Cole Matson says:

      (Forgot to mention that if there were extra miles, or if the Vancouver trip didn’t work out, I’d use the extra miles to cover my sister’s flight to Denver for the Christmas visit to western Kansas. In fact, if the miles were enough to cover two round-trip tickets exactly, I might just use them to cover both me and her for the Christmas visit to Kansas. I can always take the train to New York from Virginia.)

    • Meike Sillevis Smitt says:

      Yay for free miles!! I’m taking my daughter to Louisville, KY to see all the horses if I win!

    • Julie Garbutt says:

      This is a very generous offer. I am new to your work, only finding your blog two weeks ago. I just finished reading your third manifesto “The Tower” and the Amelia Earhart quote made me stop and think: “When a great adventure is offered, you don’t refuse it.”

      If I were selected to receive this opportunity, I would go to St. Louis, MO. See, there’s a mega corporation there that is dumping millions of dollars into my home state of Washington to influence an election regarding GMO labeling of food. I’d like to work on my legacy project, following such leaders as Vandana Shiva, to shine a light on companies that would buy elections and whose aim is to control our food system. I’d take the airfare & carry the fight to them and organize a protest in their backyard. I’ve never done anything like this before, but I am so incensed at the injustice in their campaign that I want to take personal political action. Perhaps it might direct the country’s attention to what is happening in Washington & why the issue is so very important to our future. Thanks for considering my request!

    • Pamela Whalen says:

      I would take those miles and head to Raleigh/Durham to visit my momma, Miss Dot. She is getting on in years and now that I live in San Diego it costs a lot more to visit than it used to.

    • Linda says:

      I’d probably fly up the coast to Portland or Seattle. Still haven’t visited either of them.

    • Anita says:

      The spookiest thing about this is that whilst I was reading this post you popped up on my screen doing the Creative Live preview! I live in London but would use the miles towards travelling from New York or Washington to Phoenix, Arizona to attend Pam Slim’s Body of Work 2014. I would love to be there.

    • John Williams says:

      Either Florida or New York (from west coast)

    • Aliotsy says:

      My wife and I would fly from Sacramento to Nashville so the family could meet our new baby!

    • I would use the tickets to go to New York City and Hartford, Connecticut to visit some friends out there. I’ve never been to Connecticut and my wife is from Argentina and hasn’t been anywhere in the US other than Utah, Idaho and Wyoming. As a backup option we’d use them to go to LA (for fun and to see) or Miami where she has some in-laws at.

    • R Shepard says:

      I’d book my holiday travel plans to see the folks!

    • Missi says:

      I would go anywhere. I need a vacation!

    • Daniel Villaveces says:

      i don’t usually fly Southwest either, but I trip to California to see old friends wouldn’t hurt. Thanks for the offer!

    • Ana V says:

      I just turned 40 and I managed to get pregnant with my soul mate – while we were in Mongolia! This baby has been up the highest peak in Mongolia,on the border of Gina Russia and Mongolia, on the a motorcycle trip to see eagles, packrafting 250km down a glacial stream, and now the Grand Canyon.

      While these adventures have been fun, this new mama is feeling pregnant and pooped and for ONCE I’d like to go somewhere that didn’t involve me feeling exhausted at te end of the day.

      I’d use these tickets to take my mom to Santa Fe and celebrate my 40th with her and my close friends, whom I haven’t seen in so long because of being on the road.

    • I’d take my wife to Atlanta to meet with an old mentor of mine. He’s a personal friend with a self-employment path similar to mine… just years ahead. As I transition to self-employment on Tuesday, this would be a welcome opportunity to glean some wisdom.

    • Anne Burner says:

      Thanks for the opportunity, Chris! If I won, I’d fly up to Seattle to visit friends I haven’t seen since they moved there a couple of years ago. And drink LOTS of coffee, too.

    • Linda says:

      I’d fly to Denver with my husband so we can visit our friends in Fort Collins.-

    • GARY INGRAM says:

      I would go to Scottsdale AZ for the PLF summit with Jeff Walker and also use a ticket to get to LA to partially pay for a trip to New Zealand going with my Dad who is 83 this year. Thanks Chris love your books!!

    • Alecs Variny says:

      I would love to get these miles as I fly Southwest all the time. Pick me, pick me!

    • Ashley says:

      I live in Boston, and I am from Michigan, and I haven’t been home since last Christmas…you could say I’m a little homesick! I would use the miles to buy me a ticket there now, and then another one a few months later so I don’t have to wait a whole year to see my parents like I did this year!

    • I suppose I would go to new Orleans. Southwest has a direct flight from DEN to MSY. I have been a travel hacker for over 20 years now and currently have a little over 1/2 million miles, and I swear I do not hoard them. I will be off to Taipei, Shanghai, Bangkok, Pattaya, Siem Reap, and Phnom Penh for most of November and a good chunk of December, but hell Chris if you don’t want them, I’ll use your SW points.

    • Hello Chris, Thanks for your generous offer.

      I would go to NY-Brooklyn to visit my brother, wife and niece. Until this summer, when we met for our sister’s 50th, it had been 5.5 years since I’d seen my brother and his family. Well, our father died suddenly and unexpectedly in August. Though our processing of our loss we realize we need to see each other more to celebrate the ‘good’ and happiness of family and community. My husband and I would go visit to raise a glass to the health of relationships, family and good will. We have two little boys so, with the tickets we would be able to afford to go as a family (buying two instead of four tickets) and see the next generation (the cousins-ages 8, 6 and 4) connecting, growing and celebrating.

      Thanks for the opportunity! Also, looking forward to being a part of WDS again next year! Yay!

      Audrianna Gurr

    • Michael T says:

      My wife and I’s anniversary is next month but don’t have the time and funds to do anything worthwhile. Would love to go to NYC to visit some family and friends and see the city.

    • Andrew says:

      What a great thing that you’re doing!

      My use for the points is purely selfish.

      I’ll be using them to travel LAX to PDX to attend WDS2014 for which I have a ticket.

      I’d only have to scheme ADL to LAX if I had the Southwest points. Incidentally, we travel Southwest as exclusively as we can when in the US – great comparative prices and two bags!

      Tally ho …

    • Tiffany says:

      I’ve always wanted to visit Oregon. I have friends who live there, went to uni there and now have families there but I’ve never been able to visit due to spending money on flights back home to see my family. I would love the chance to visit Portland and then drive to all the beautiful woods and lakes and experience the wonder that everyone raves about! Thank you!

    • I haven’t been home to visit family in two years, and won’t be able to make it until July 2014 thanks to work commitments. Would love to be able to visit family somewhere in the US from the hub at Midway Airport in Chicago!

    • Lisa says:

      This would be fabulous – I gave my son a trip to NYC for his 21st birthday and these tickets would get us there to celebrate in style!

      I just go the hilton card so I have 2 free nights at the waldorf coming up – the perfect place for a 21st bday celebration!

    • Irina says:

      Oh wow! people have some really good reasons to get those miles… I would be using them just for my personal enjoyment and not for a real need. So I just wish every one good luck while I sit this one out. What you are doing here, Chris, is special!

    • Matt says:

      Haven’t flown Southwest since they moved in at ATL. I’m thinking Vegas could be in order later this fall.

    • Thomas Eliot says:

      I would use the tickets to take myself and my girlfriend to Texas so I could propose to her in front of her parents.

    • Cathy Luders says:

      Hi Chris – I have been following your blog since 2008. I have written my personal manifesto and have purchased British Airways cards for miles after reading one of your blogs a few years back. I asked you for help and you suggested Iberia and it worked out splendidly well! We used the miles for our 30th wedding anniversary trip to Italy! Now my elderly father moved in with us when my mother died. I am blessed with brothers who step in and take care of my dad so my husband and I have some time alone – such as this recent trip. I would use the miles to ensure my dad could spend time with the one brother and family who live in Jacksonville, Florida. This brother’s job takes him all over the world and he has had less time with my dad since he also has two young children who need him when he is back on US soil. Thanks for the opportunity. Whether I win or not I intend to keep listening and acting on your advice and also buying your products as they come out! Blessings on your journey!

    • matej says:

      I would use ticket to visit Yosemite while im in USA for the first time in my life πŸ™‚ ( April 2014 πŸ™‚

      thanks for chance to get this nice reward and thanks for great newsletter im recieving last few yrs.


    • Mike Kent says:

      My wife and I have always wanted to go to New Orleans…:)

    • Benny says:

      We don’t have that many direct flights out of Jacksonville on Southwest, but they do go to Las Vegas! So that’s where I’d use the points.

    • Chea says:

      Wow, what a wonderful gift to give! If I’m the lucky one I’ll go to DC and NYC for much needed major art infusions – visit all the galleries and take my pal, who’s never been to the Smithsonian. We’ll get some eye-gasms!

    • Terri says:

      Great giveaway! I’d use the miles to fly to Nashville, TN. A very good friend recently got engaged, and that’s where she’s getting married next year. She was in my and my husband’s wedding, so I hate that I can’t even attend hers. But we have a one-year-old, recently moved, and have to travel to attend my brother-in-law’s wedding in June–it’s just not in the financial cards. But with those miles, it could be!

      I’ve also just always wanted to visit Nashville. My husband works in local music, and I love checking out other cities with great scenes and musical history.

    • Wes says:

      I will be flying to Los Angeles with my fiancΓ© to get married July 6, 2014. We also plan to fly out to LA for engagement photos in December. With these miles we would send pics to you to share with everyone at AONC.

    • Veronica says:

      I would go to Norfolk and then wander around the chesapeake bay area with my family.
      I don’t know that part of the country and would love to explore it more.

    • philip says:

      I would go visit my best friend in DC. Bros gotta hang.

    • Jessica says:

      I would fly to New Orleans to visit a college friend that I haven’t seen in two years (she just got back from completing her MFA at St. Andrews in Scotland). I’d use the second ticket to fly in a friend from Texas for a ‘college reunion.’

      Also, as a blues dancer, dancing the blues in NOLA would complete a bucket list item.

    • Tamara Seiler says:

      There is no sweeter place, than Portland in July! And I don’t know if you’ve heard, but there is a group of crazy people that take over the city for 3 days and dominate all of downtown through creating community, adventure, and serving opportunities. Its pretty freakin amazing πŸ™‚ My husband and I bought our tickets as soon as we had the chance because we were not going to miss the 2014 dance party and all the epic surprises that await! We just need to book the tix and Southwest is great since we have to fly out of Omaha.

      Thanks so much for offering to share your miles with AONC peeps:)

    • Karen Heumann says:

      Chicago, baby! Summer 2014

    • eleni says:

      HI! I’d go to Maine. Haven’t been there yet. I love the U.S. and all it’s diversity. Why would Geo. Bush want to have a home there? Must be something about the state and it’s remoteness that draws a certain type of people who can afford to hide. I’ll be the born and raised Maine – ians are worth knowing!

      this was fun! thanks!

    • taylor says:

      This is an awesome giveaway, Chris. Thanks for the opportunity. I would use the tickets to fly to Denver, Colorado for an snowboarding trip in January.

    • Chioma says:

      Chris! Thanks for the awesome contest! Easy-peasy answer: ticket one to go and see one of my soulmates in NYC – we used to live together in Tanzania two years ago and haven’t seen each other (aside from Skype) since! The second would be to go to Louisiana – I was born there and have never been back since…so it’s not only about the Beauford boils (okay, fine, it’s 50% about the food..)

    • Lonnie says:

      Your generosity knows no bounds. Congratulations to whoever wins!

      What would I do with two tickets if you pick me? I would take my best friend to Florida. The Tampa Bay area. She’s never seen a Dolphin the wild, or curled her toes in the white sands of Sarasota and Siesta Key. There’s real magic in that water. Life slows down, stress melts away, and adventures await. There are hidden spots you can see manatees playing in the water. The vitamin D from the sunshine is worth getting away from the grey skies coming.

      That’s what I would do. Good luck, everyone!


    • Christy says:

      I’d use the miles to go to LA – we have a sister who recently moved out there and a friend who’s turning 40 in January!

    • Delia says:

      I’ve been pretty sick since 2005. I’ve made a great deal of progress during 2013 and I’m almost ready to rejoin the world.

      First choice: I’d use the miles for my husband and I to follow the Atlanta Braves during the MLB playoffs. If it’s too late to book those trips, I’d love to go with him to San Francisco, where we honeymooned, then to New Orleans (I’ve been there before but I spent it in the hotel after eating something to which I was allergic), then home. He’s the national chairman of Crimestoppers of the United States and works *really* hard, and he deserves a break with a wife who is healthy and able to travel. It’s the first time in 8 years I’ve been able to say ‘let’s go.’

      Thanks for the opportunity.

    • Jacob Herman says:

      Ski seasons coming up.Flights to Colorado to visit a friend who moved out there a few years back. We will wake up early and skin up into the mountains trying to find that untouched powder. Snow as soft as my furry beard.

    • D Michael says:

      With the tickets my Art + Money business partner will fly to NYC from Portland and kick off a coffee house tour throughout New England to promote independent artist work online. This new artist support business will use the Art of Nonconformity strategies to assist artists with marketing their work. Thanks Chris and everyone for building this great community!

      D Michael Workman

    • Tracey Surine says:

      I want to win! I want to go somewhere, anywhere. It has been twenty years since I have been able to travel and will probably be ten more… long story (4 children… 3 in college…)

    • Laura says:

      Chris, this is a wonderfully generous idea: thank you so much for the chance to win these tix.

      I’d head for New Orleans. My husband worked the season as a jazz musician in the 1990s; we shot a series of photographs from walking/wheelchair user perspectives. I would love the chance to recreate the series post-Katrina. (He hasn’t been back since the storm… I better have a Sazerac handy to revive him.)

    • Josh Hill says:

      Hi Chris,

      I’d take my girlfriend from LGA to RDU and then drive to Asheville. We’re working on getting her to all 50 states πŸ™‚

    • Chris Allen says:

      I would go somewhere new. Maybe the southwest or east coast.

    • John says:

      Charleston, SC for my upcoming family reunion!

    • sKY says:

      We’d like to fly somewhere we have never been before. Somewhere warm to go skydiving, like California, Florida, Vegas or Arizona. I love the thought of settling in to a week-long spiritual retreat in Sedona. Or a wine tour in Napa. Or a weekend of hiking and camping in Yosemite. So many possibilities!

    • Sarah says:

      OMA>SLC or maybe OMA>PBI. Depending on whether I’m feeling selfish (Ski Utah!) or caring (visiting sick, old relatives in Florida) that day.

    • Veronica Pacini says:

      There are so many places I could go with 50,000 miles. Since I am currently starting a new business and am not yet making much income, these miles would make it possible for me to travel to see family and friends in Fort Lauderdale, FL, Albany, NY and/or Washington, DC. Which would be so AWESOME! Thanks Chris for sharing your miles – for whoever wins πŸ™‚

    • I would go to Seattle, Washington to film a new Ginger friend I just made through the interweb thanks to Skype and someone for nominating her to be in my documentary, Ginger Girls.

    • TSP says:

      To visit my sister in Seattle.

    • Terrah Mayes says:

      November first will be my forty first birthday. I am not picky. I just want to experience some place with a beach. I grew up in Seattle and have lived in Utah for too long now. I have had a rough few years. I would love to see the Atlantic ocean. I just want to experience culture and beach and something new. Perhaps it will spark my creative side once again. That block has lasted too long. I also want to attend (Die Empty and DWS 2014). I will help with Photography, marketing, advertising and any other nonmarketable skill that will help. I miss the beach. I miss my free thinking self. I would love to experience something scary and completely out of my element and a beach- you pick- I will travel and blog and interview random people about what they love about being alive and are they living their dream life, if not-what’s stopping them. I would love to spend Christmas Break there- Wherever or over new years. Just for the experience and the culture and to meet new and interesting people. I am not sure if I actually have a shot…But I am definitely one of your non-comformist army members. I hope you pick me, but if not we will meet at some point. Thanks, terrah

    • Cyd Peroni says:

      This is fun! Thanks for sharing your miles. I’d definitely use them to go to Portland for WDS 2014. This will be my first WDS. I’m so psyched about it that I’m feeling like anything is possible – even winning your miles! (I’m feeling so lucky because it’s been a great week for creative projects around here.) Plus, it would make my husband really happy because he doesn’t know I spent the money for the tickets to WDS yet. Ah oh. πŸ™‚ If the miles need to be used in 2013, then I’d definitely visit my nephew in San Francisco. I visit him every year, and it’s time! Thanks again! Good luck to all!!

    • Two free tickets? I’d take my husband away somewhere for a break – anywhere that he doesn’t usually associate with work, and preferably somewhere with minimal cell reception!

    • David Bentler says:

      Thanks for the exciting opportunity, Chris! I would love to take my girlfriend to New York City during the fall. It would be a fantastic place for a potential proposal! What did Sinatra say?

      “If I can make it there
      I’ll make it anywhere
      It’s up to you
      New York, New York
      New York, New York”

    • David Andreas says:

      New York would be my choice. I have never been and I have friends and family that I would love to visit. Thanks Chris!

    • Mindy Holahan says:

      Todd’s book is fantastic! Thanks for sharing it with your audience, it’s great work. And thanks for sharing miles, it’s a kind gift! I would fly into Atlanta and drive to Savannah for New Year’s, for no other reason than it sounds beautiful and I’ve never been to Georgia. I’ve read a few books set there, and it sounds like a place to be experienced.

    • Hi Sean!

      I would fly to Washington D.C. and travel the DMV area. I have wanted to move to the East Coast for many years. I am actually taking steps forward into the life I really want to live now. So, I would take a trip with one of my besties (who also wants to move there) and so I can have a better vision of my life there. Check out areas to live, transportation, fun things to do, etc.

      Thank you for the opportunity!

      Sincerely, Nancy-Marie πŸ™‚

    • Jim Salmon says:

      What a unique opportunity for someone. Personally, I would use the miles to take my wife and me to San Diego. It’s one of the few places where we both feel like we could live there. It’s on our list to return sometime for an extended stay.
      No matter what, I so enjoy your slant on the life you (and the rest of us) have been given and wish you every success that you pursue.
      Thanks for all you do!

    • Delores says:

      I would take my hubby and hightail it to Portland where he can collaborate with his best buddy on his new idea for a book and public radio coverage for a local fine arts festival.

    • Shawn Turpin says:

      I would love to send my mom on a trip. I am teaching overseas and she helps me out in so many ways while I am away from home. She takes care of my college age kids when the need arises and this is the biggest blessing to me. I would love to show her my appreciation for all she does!

    • Melissa says:

      I’d go to Tampa Bay! I have a colleague who lives down there and works remotely and he’s ended up being one of my best friends for over a year now even though we have never met in person. We have gotten each other though so much this past year, always sending support to each other through bad days, relationships, jobs, fitness goals. I would love to visit him and try some of his amazing vegetarian cooking and finally have the opportunity to express my gratitude for knowing him face to face.

    • Stephan says:

      I live in Munich, Germany and would go to Vancouver, because I’ve never been to Canada and I have two friends there who don’t know each other and whom I haven’t seen for years. Get them together and see them again.

      On my way I would stop over in Montreal, to practice my French and because I’ve heard that it’s a beautiful City.

    • Ted says:

      DTW-SAN in the middle of the winter πŸ™‚

    • AJ says:

      I love you man!

      I’d use the miles to take my buddy (a HUGE Denver Broncos fan) to a game at Mile High. The Broncos have a great team this year, and it’s been on his bucket list to go to a game.

      I think that’d make me the best friend in the universe no?

      Keep up the inspiring work!

    • How wonderful of you to offer these tickets! Personally, I would like to fly down and visit my Mom in TX for a long weekend- twice. It’s hard for me to get away for long so a long weekend would give my my “momma” fix and having the chance to go twice within a few months would be amazing.
      Thank you for running this contest- good luck to everyone commenting πŸ™‚

    • Hi Chris – I’ve got all kinds of places that I would visit:

      St. Augustine because I’ve never been there
      Boston to see my college roommate
      Denver to visit one daughter
      Chicago to visit another daughter and my brother
      Washington DC to visit my sister
      Albuquerque because I’m crazy about New Mexico
      Phoenix to visit a dear friend

      Thanks so much for making this offer!

    • I would take my husband on a trip from Manchester, NH, (we live in Maine) to San Francisco, CA in celebration of twenty years of being together as of November 20th.

      We were high school sweethearts and are best friends who spent years traveling together. Then three years ago we had a baby and it turns out she doesn’t share our love of traveling! She literally wakes up for the day at 1am or 2am every single time we try to go anywhere. The loss of travel has been devastating, not to mention the loss of time to be just one-on-one with each other. We love our little girl and are beyond grateful for her (we went through a lot to have her) but my husband deserves some of my focused attention on him. Finally! We’ve never been to the west coast and often talk of doing it someday.

      We can’t afford to make it happen for ourselves because we’re both educators, and his public school is taking 35% of his GROSS pay for health insurance. To say it’s been tight is an understatement.

      Thanks for this opportunity!

    • Patty says:

      A big hope here as since I moved to the South and family in the Lake Tahoe and Sacramento area I have not seen them for years. I love Southwest but being a very small business, age 66, person I can’t afford the passage. I truly hope someone receives this generous gift who can use it for good reasons. From a grandmother that misses her granddaughter and homeland.

    • Rhonda says:

      Hi Chris! This is an amazing opportunity!

      My husband and I would definitely put the tickets to good use. We would fly Southwest to Seattle, after stopping at Pike’s Peak for some chowder that I hear is a must and a tour of the Japanese garden, we’ll take a ferry into Canada and finally get to use our passports!

      Best of luck to everyone who enters!

    • Elizabth Matney says:

      What a wonderful offer Chris. Thank you. My partner and woud use the tickets to fly to Portland for WDS. First time! She needs a break from academia and I want to expand my mind and community. Portland in July it would be!

    • Justine says:

      My boyfriend and I love traveling, but have never seen the Pacific Ocean before. We’d totally go from Philadelphia (he’s never been, and we live in NJ!) to San Diego to check out La Jolla, San Diego Zoo, Torrey Pines and of course… local restaurants.

    • Becky says:

      I always fly Southwest to visit my mom and step-dad in Florida (I live in PA). I’d love to use points to see them around Christmas this year.

    • Terri says:

      I’ll go anywhere I want to, wherever the wind whispers to me the day the gift is given. -no boundaries

    • Max Tite says:

      Our son is in the middle of France for eight months; his girlfriend can only stay for a few more months (no work visa), so we would Love to go and visit him sometime shortly after the holidays! I think that’s where we would most like to go right now…

      Thanks for this opportunity to dream about that opportunity!

    • Chris Oakes says:

      50,000 free miles would be awesome – my wife and I just made the West Coast and we’re hoping to hit the East Coast very soon due to our new travel hacking schemes! Thanks!

    • Audrey says:

      My best friend who lives in Orlando just received some crazy, stressful news. I am near DC. I would fly us both to Albuquerque for a long relaxing weekend in the Southwest. Navajo Tacos? Art Galleries in Santa Fe? A quick visit to hike around Angelfire? I can’t think of anything better to take some of the pressure off and get her ready for what lies ahead.

    • Angela Henry says:

      This is such a wonderful thing for you to do for your fans, Chris! I would pack up my overworked, single mother sister and go to San Francisco. A full time mom, mortgage broker, meal making extraordinaire, and nursing student, I have never met anybody more in need of a break. I could take care of the rest if our flights were covered. There, we would visit with my best friend Keith, drive along the coast and watch the sunset in Carmel. A fantastic man I have not seen in 6 years, who lives in Napa Valley and is a chef. It would mean the world to us, but if we do not win then this is still a wonderful gift to put into the world.

    • Christian Hauser says:

      I’d sprint home HOU-BHM for spring break and take my soon-to-be brother-in-law (15ys) to Vermont on a backpacking trip.

    • Todd says:

      I would travel to Chicago, Vegas, Miami, or Angel Fire, NM. Yes, a lot of places to go. πŸ™‚

    • Sarah says:

      Thank you Chris! This is very generous of you. I would surprise my nine year old daughter with a trip to Charleston, SC. Neither of us have ever been to the south and would love to see a different part of the country from our home in the Pacific Northwest. It would be a grand mother-daughter adventure. Thanks!

    • Sarah says:

      I would use these to go to NYC with my husband for our 15 year anniversary. We lived in New York for 7 years at the beginning of our marriage and we have not been back even for a visit since we left!

    • Felicia says:

      I would fly to Portland with my sister for a last big trip before we both move out of our home state, Missouri. I’m trying to get to all 50 states before 2015 and Oregon will be number 44!

    • Abigailia says:

      I’d use them to fly to Mississippi and visit my friends I haven’t seen in two years since I moved back to California. It’d be so nice to see them!

    • Chris Norton says:

      After reading your blog for a couple years, and a short stint as a member of the travel hacking cartel, the most poignant take-away I’ve transferred to my own life is your annual review process. The first year I did it in 2010 was a bit of trial and error, and ever since I’ve refined the process and included my own additions tailored to my life. I truly believe that if you don’t have any plan, you’ll get somewhere, but not necessarily where you want to be. Three years ago I was unhappy in a cubicle, and now I work completely remotely and the annual plan is a big reason why I was able goal hop and transition my life to allow for me to be much happier. This year instead of grinding the hours away in my cubicle during the December holidays, I’ll be cycle touring for charity (affordable housing) with friends from Orlando to Fort Lauderdale and then continuing on my own to Key West. I currently do NOT have a return flight booked, and Southwest is one of the few airlines that offers tickets from Key West back to Boston on my return date of January 6th, 2014.

      Good luck everyone!

    • Kim says:

      Since our son was born, my hubby and I have traveled significantly less and haven’t flown anywhere. We would travel to Boston for a weekend away to explore the city together.

    • Shaun Somers says:

      Until looking at the route map because of this post, I didn’t even know SouthWest flew to Seattle! That’s where my wife and I would go if we won. Never been to that part of the country, and close enough that we could visit with my sister/sister-in-law who live in Vancouver BC.
      Thanks for the contest!

    • Andi says:

      I would fly to Cali and do a really long road trip up and down Highway 1, maybe even dip down into Mexico.

    • Kyra says:

      I would use these miles to take my husband on our honeymoon (finally)! I’m trying to infect him with the travel bug and I want to show him the beauty of the Pacific Northwest or the Florida Keys. Thanks for putting the miles out there!

    • Ariana says:

      Hi Chris, I follow your blog because a former co-worker of mine told me about it, and after reading one post I couldn’t get enough. I work for a website that helps people raise money for their out of pocket expenses. Many of them are facing cancer and other serious illnesses. If you gave me the miles I would find a family on the site who needs to travel to treatment and give the miles to them. Your stuff is great. Thanks for keeping me inspired.

    • Jalyn says:

      My wife has never met my dad’s side of the family. So I would whisk her away to…Oklahoma. Not even kidding…..

    • Janet Lee says:

      First to Charleston because I have never been there and it is on my Bucket List. Then to Chicago for some Garrett’s Popcorn! Thanks for the opportunity to dream.

    • Aesop said “adventure is worthwhile” and I take that to mean flying Southwest for free (courtesy of Chris Guillebeau)!

      I live in Salt Lake City so it’s easy to fly Southwest. I’d take my sweetheart to San Diego to get some much-needed breakfast pancakes at Richard Walker’s Pancake House.

    • Brandon K. says:

      I’d probably go home to Atlanta or maybe adventure out to Denver. Who knows! The possibilities are endless!

    • Mindy Robinson says:

      I would love, love, love to get 50,000 miles! I’m saving up now to buy your books and start travel hacking myself, and this would be an awesome jump start!!!

    • Hilary says:

      I always fly southwest!! It is the only airline that offers non-stop between TPA-PIT. I got a s-west credit card for that reason! I would take my mom on a trip to San Francisco!

    • craig says:

      Great site, I use it mainly to try and inspire my kids to ‘break free’.

    • George says:


      I would use the miles to fly from Midway Airport in Chicago to Fort Lauderdale, Florida to visit my brother. He is in school there by himself and misses his family! Also, the fact that it is beginning to get cold in Chicago helps too. πŸ™‚

    • Kathy says:

      I would get far, far away from the winter rains of the pnw (across the river from you). Thanks, Chris, for this and all that you do!

    • Casey says:

      Hello Chris! wow- that is awesome you’re offering a Southwest trip- thank you for your generosity. πŸ™‚ I’m currently in Northern CA and I would choose a destination as far away as possible so that leaves me with Boston (oh yea!) or Ft Lauderdale (mmm waaaarm!). Tough decision to make but I would most likely chose Boston.
      Good luck everyone!

    • Alison Van Hoy says:

      You = Inspiring. Unique. Empowering. A Revolution.

      You continue to inspire me in the travel world, and I’ve been to your around the country book talk which was also inspiring. I’m a native Oregonian, and still live in Portland. I have told many people about your book, and to say you’re local is amazing! I want to keep this awesomeness (I know that’s not a word) going, and write about my next adventure with the travel miles.

      I’ve recently decided to make it to every continent by the time I’m 30. The only problem is Antarctica can be hard to get to, but I know it’s possible. These miles will get me to Argentina, where I can get on a cruise from there. An absolute dream come true, I’m going to make a travel journal about all of my adventures (inspired by you).

      I would absolutely love this opportunity, and know I can inspire others just like yourself!

    • Jen says:

      BOS-STL non-stop! It’s my first year of grad school and I am missing my family and wiener dog!

    • Mihir says:

      I would give my wife the opportunity to fly to wherever she wanted with a friend of her choice. I travel a decent amount for work and, while I’m away from home it’s not easy for her to take care our two boys alone (one in school, one in day care) and also hold down a full-time job. She more than deserves it. We live in Columbia, SC, so departure airport options are Charlotte, NC, Greenville-Spartanburg, SC, and Charelston, SC, all within 1.5-2 hour drive of here. If I had to choose a city she might like, it would probably be in California – most likely the Bay Area as she’s been wanting to visit Napa for a long time.

    • Amie says:

      Oh wow! Well, I am planning on presenting a SHINE conference (the under 25 girl’s portion of a women’s conference) in Australia next year. They don’t have the budget for a plane ticket, so I would apply the miles to the US portion of the trip and save myself some money! Thanks Chris and best wishes to everyone in this rockin community.

    • Joe says:

      Hey Chris, thanks for being so generous. I would use the tickets for a trip to Belize with my son Dyllon. He is a senior this year and both he and I have always wanted to visit Mayan Temples. We both love adventure and this trip is what I’m planning on giving him when he graduates. Thanks for the awesome chance! I wish everyone best of luck!

    • Alan Bailey says:

      Thanks Chris for offering this. Where? I would give the trips to my wife to visit her 89 year old father who just lost his wife .. and had a stroke last year. Tampa, FL .. she really needs those miles .. and those flights.

    • We have been wanting to visit our very good friends in California. I could really use two tickets to Ontario or Burbank, CA.

    • Mirva says:

      I would fly to San Diego to visit my old college classmates and other friends. Despite constantly being on the move and traveling to random remote places, it’s been nearly a decade since I last made it to lovely SD!

    • vicki says:

      Thanks for your generosity πŸ™‚ I would love to win the tickets so we could fly to NY and visit my best friend…we haven’t had an opportunity to visit her since she moved and we miss her family dearly!!

    • Jasmine says:

      Thanks for all that you do and for being so generous with your miles/points!

    • Claire Soloski says:

      I would soak up some jazz in New Orleans and then soak up some love and sun visiting my family in San Diego.

    • Rocco says:

      Chris, I’d use the miles to viist my mother on th east coast outside of Hartford, CT. Thna!

    • Nubiaska says:

      Chris, awesome offer as per usual. Recently laid-off and would love to use this very generous gift to show my 14 year old daughter more of this beautiful planet! She’s an amazing soul and just started high school. Been a bit of a struggle of late but I’m determined to use circumstance as an opportunity. My little girl never complains and deserves all the world has to offer. I want her to continue to expand her horizons through the best education available………travel. Thanks to you.

    • Glenn says:

      Chris — My wife and I recently ‘celebrated’ our 20th Anniversary by “hoping” for a trip to Montana. I know Southwest doesn’t fly Detroit to Montana, but Boise, ID is close enough.

      I’ve had various jobs over the last 7 years that required me to travel all over the country, neglecting my family while earning points through airline and hotel clubs but never enough from just one to really earn anything of value. Maybe a random hotel night when taking the kids to a soccer tournament, but nothing of significant value (mostly because these employers had restrictions on where to stay and how to book while I haven’t had the credit worthiness to get any of the cards you recommend).

      Why would I want to do more travelling? Because it’s something for my wife who has put up with my crap and not really being home much these past years. Even when we could go somewhere as a family, it was either to Florida for my work or New England to see my family — neither really giving us a true vacation!

      As much as I find the idea of Montana fairly boring, I know it would be something my wife would remember forever.

      Thanks for the opportunity.

    • richard says:

      wow this is a lot of posts. I would visit my brother and his family in ohio. he is the only one of us kids not in the Utah/Colorado and so none of us go his way. I know it would mean a lot to him for someone to come visit him.

    • Debi Wandrey says:

      So very generous of you!!!

      Back in January my father-in-law contracted the flesh eating disease. He miraculously lived without loosing any limbs, but has had months of hospitalization, surgeries, skin graftings, etc. He has always been an active man, but now is not able to travel like he used to, so we aren’t able to see him like we’d like to. He is 78 and also just had his hip replaced. My husband and I really miss him. He is our only father between us. Mine died when I was 35. We have no mothers either, as they have passed as well.

      We own our small business here in California, and could make the time to go see him. We’d love to go in early November. I know my plea isn’t the only one, and many are very worthy as well, but it would be an honor and a privledge to accept these points from you.

      Love your website and books! Keep up the good work! And God Bless you for choosing us:))))

    • I would use the air miles to decrease my business expenses to I can give more back to those I work with in Africa.

    • Cathleen says:

      I’ve always wanted to visit the Pacific Northwest, so I’d fly from BWI to SEA, take a jaunt down to PDX, and maybe back to BWI via SLC. That can totally be done w/50k from SW on a good day πŸ™‚

    • Ok I did not look at the map…they fly in the states…I would use the miles to go to Virginia to do a workshop for this Fairtrade Business that I have just connected with…this will be a business expense but will not take away from the social entrepreneurism of my business.

    • I’d fly to Phoenix, which is as close as I can get on Southwest to the Grand Canyon. It’s been a year since that gash in the earth healed me of a desperation and depression and started me on a new path to volunteering at National Parks. I want to stand barefoot on its rim and watch its unforgiving magic through tear-sharpened eyes. I want to walk into its healing core and touch its rock walls, to let my insignificant human hands say thank you through the rock. I want to look into the eyes of every other hiker I meet and feel that electric leap between us that says, “The Grand Canyon!” I want to smile at everyone until my cheeks hurt, just because I’m there again, in that place that showed me what really matters in my life — living by nature’s uncompromising rules, not man’s made-to-order laws. I want to spread to everyone the indescribable joy of being in that incomparable place, and watch that joy smolder through them like a wildfire. Thanks for your generous miles offer, Chris, and for giving me the opportunity to turn my thoughts back once more to a life-changing event.

    • Laura Hosley says:

      I would give the miles to my daughter, Jessica. She graduated from Long Island University’s Global College in May and has been a kayak and biking guide in Acadia Park and Bar Harbor Maine since. She lived and studied in India, Costa Rica, Nicaragua, Thailand, Turkey, Taiwan and New York City during her college experience and, as a result, is now an open-minded, aware and motivated adult. I visited her in as many of these countries as I could and was amazed at her confidence and independence. Can you tell that I am proud of her?
      She has never been to the west coast of the United States, except to fly out to Taiwan, and has a friend in Portland, Oregon that she has said she would love to visit. I think it would be great for her to experience the other side of the country, since she was born and raised in Rhode Island. She is not sure about what she wants to pursue now, with her degree in Intercultural Communications, but she’s young and I encourage her to continue to explore and enjoy her adventures.
      Thank you for the opportunity to potentially win the miles to get her to Portland. I guarantee she would utilize the opportunity to learn more about the area and see the possibilities.

    • Kevin Dudley says:

      hahahaha……I could never compete with most of these people……and I don’t even know if conversion is possible but, I’ve been trying to get to Ghana to work with my “brother from another Mother” to build our orphanage, medical facility, elder care facility, and school in the northern sector……we send funds all the time but, they really want me there to make the big things happen…..miracles are possible when people believe…….bless you and keep doing what you do…..

    • Laura Ostrem says:

      I would fly to Jackson MS to visit family. Thanks for giving away your miles!

    • Alexzandra says:

      My husband and I would take a trip to San Antonio after our baby is born so that she can meet her grandparents, aunts and uncles for the first time!

    • Shannon says:

      I would use the miles to check off items on my bucket list! First to Utah for the Sundance Film Festival & to NYC duing the holidays!

    • Baird Kleinsmith says:

      Thanks, Chris! I’d fly my wife and I to see her grand parents in FL. Need to take any chance to see them while they are still here and healthy!

    • I would use the miles to take my friend and I to L.A. We both want to make a big career move and are in film/comedy. He has never been to LA, I want to LIVE there for a shot while to see if it’s really for me. We’re both ready to take that big jump.

      Also, if anyone comes to Brooklyn, let me know. I can host or possibly give you a tour.

    • Gael Chabot-Leclerc says:

      I would go to San Francisco or to WDS next year!

    • Roseanne says:

      Hi, Chris,

      If you’re able to book July tickets in Nov, I’ll choose to go to Portland to the WDS for sure! If not, I’ll choose somewhere in a state I have yet to explore, like Washington, and fly in and out of Seattle. Thanks for your generosity and sharing how you think out of the box.

    • Jen Radicella says:

      I love flying Southwest! It has been far too long since I visited New York.

    • Claudia Telles says:

      Hi Chris,

      Thanks for your generosity. With the tickets I will go to Vegas with my sister to celebrate my Master’s Graduation in Public Health Policy as well as her 21st Birthday.

    • Jim E says:

      Thanks for the giveaway! I would use the miles so that my wife and I could visit our family at Christmas (HOU to DEN)…thx~!

    • Becky says:

      Houston to see my wonderful family.

    • Rebecca says:

      Thank you for offering your miles! I’d definitely go see my family in Houston, and maybe try to pair it with Formula 1 in Austin, some wine tasting in the hill country, and a nutrition seminar in Dallas. Lordy I’ll stay in TX a month, ha ha!!!

    • Ben says:

      My wife and I would go to San Fran. When using miles we always try to go as far away from home as possible. Coast to coast, baby!

    • Nancy says:

      My favorite places to fly on Southwest has been New Orleans! So one ticket would be for another trip to NOLA! And the other ticket would be for Houston, where my good friend moved back to. I miss her terribly and would love to see her.

    • Kishor Rao says:

      Would love to take the wife on a vaca to Florida or Vegas!

    • Christina says:

      What a fantastic giveaway. I would use the miles to escape winter in Key West. For the second flight I would be ecstatic to finally make it to PDX.

    • Ryan B. says:


      I am stationed in Wyoming with the Air Force and only get to see my fiancee about once a month who lives out in Southern California. Thankfully Southwest has a great nonstop flight from Denver to out there that we use as much as we can, but with work and everything it can be pretty tough.

      These miles would greatly help to bridge the gap in our Long Distance Relationship!

      Thank you!!



    • I would cover as many of these quick weekend trips on my horizon as possible. To Toronto to see the Dixie Chicks in November, to AUS to see my niece and nephew for his birthday in December, to FLL as a way to snag a cheaper flight to the Caribbean this winter. Note: since my home airport is AVL, I will fly out of GSP. Thanks for doing this!

    • Kendall Burton says:

      I will take my 5-year-old son to Atlanta, Georgia, to meet his biological family and join them for Thanksgiving. Best Wishes, Kendall

    • Hi Chris!

      I would use the miles to fly to Italy with a friend of mine. She recently showed me pictures from her trip 3 years ago and it further fueled my thirst for adventure.

      Thanks for your generosity!


    • Christy says:

      Hi Chris,
      I would fly me and my new husband down to San Diego where we would meet my in-laws, cross the border, and meet Oscar’s two brothers in Tijuana. We would take a bus down past Mexico City to meet the extended family that I have never met, but only heard great stories about. We would tour Mexican cities and towns, eat fresh salsa and tacos from food carts, go to museums that displays the local history and culture of the country, the food and art.
      Then we would rest and smile.
      The following July my points would go to Oscar’s brothers and their families, where I would fly them to PDX. I would pick them up at the airport and drive them down to my barn house in Willamina. Walk down to the Wildwood Hotel where I hang out with my friends, drink local microbrews and listen to top notch, good music. My husband and I would take them to Newport to go crabbing off the pier, then to the Bay to watch the Shrimp boats go out while we drink Dutch Bro. coffee while listening to the Harbor Seals bark while we walk. We would go to Portland to enjoy the gardens, museums, art, and city life and of course eat a maple bacon bar. Then we would rest and smile.
      Much appreciated Chris!

    • Cy says:

      Thanks for the opportunity!

      I’d use the miles to take a trip to New York City with my mom. She absolutely loves Broadway, but doesn’t like to travel on her own. Some of my best friends live in the city and I’d also love to see them.

    • Monica says:

      I would go to New York and actually spend more than 2 hours there this time! I’ve been only once for a flight transfer, and it wasn’t very pleasant since I lost my luggage. I have friends over there I’d like to visit too!

    • Quinton says:


      Thanks for the generous offer. i would use the tickets to take my lovely wife to Washington/Oregon. She is German and that area of the country is more like Germany. Thanks for this opportunity.

    • I moved across the country (away from my family) this summer to live in the most awesome city ever (PDX, duh!). I would love the opportunity to be able to fly back east to visit my parents. You continue to be awesome!

    • Meg D. says:

      Wow! How generous! If I were to win, I would give the tickets to my sister. She works hard, is a single mom and doesn’t get to travel much. I bet her 12 yr old son and her would have a great time deciding where to go.

    • Linda Chreno says:

      Thanks for a great contest – and what fun reading where people would go with their miles.

      I have been watching Breaking Bad so I want to go to New Mexico – Albuquerque to be exact!

    • Hugh Hunter says:

      I am working on a project about Hope. I have a blog where I post photographs and conversations with all kinds of people that I talk to about the meaning of Hope. I want to go to Maine to talk to Robert Indiana. He is the sculptor that did the original Love piece and later did the Hope piece during Obama’s first election.
      Thanks for what you do Chris!

    • Leila Tite says:

      Hi Chris,
      My husband and I would love to take advantage of these miles to spend Thanksgiving with our daughter and her husband, who are teaching disadvantaged kids in rural Mississippi as part of the Mississippi Teacher Corps.
      You are awesome! I’m sure whoever wins will be very happy and grateful!

    • Ramsey says:

      Thanks for the contest, Chris!
      I would use the points to visit family in PDX. There’s a soon to be one-year old baby that I haven’t gotten to meet yet.

    • Nikki says:

      A year ago I met two amazing people and we became fast friends. Even though we were only together for 3 months, it was the most intense moment of my adult life. We all just clicked like we were all suppose to be in each other’s lives. Then they have to move back to California and I haven’t seen them in more than a year. I would use the miles to fly to California and reconnect with them. It’s a rare thing in life to find great friends and I refuse to let distance get in the way. Thank you for offering this generous gift.


    • Kevin O says:

      I would go to Las Vegas for me and my girl.


    • MEGAN says:

      Duh!! Pick me!

      I want to go to Brazil to watch the World Cup!

      #nobrainer #yourenice #bff

    • D says:

      I would use the miles to fly to my parents house for the holidays. =)

    • I just moved to Ireland for college and I would use the miles to help me get home for the bluegrass festival I help to put on! It’s not nearly as much fun putting on an event if you can’t go to it!

    • Donna Manley says:

      In Memphis, we are just recovering from many years of horrible airfares. Since Delta has now removed Memphis from it’s list of hub cities, the door is now open for Southwest. We have often driven to Little Rock or Nashville to get the decent airfares that Southwest has brought to so much of the country. Soon we will be able to move about the country from the convenience of our local airport. Thanks for offering this.

    • Josh says:

      522 COMMENTS?! I have no chance!

      I have two options, but I’ll let you pick the trip if I win:

      1. Fly IND to TPA with my Father, in order to finish off my baseball stadium quest (which you know something about!). Seeing the Rays and a side trip to Miami next spring would complete my quest for all 30 teams.

      2. My oldest daughter turns 5 in February. I would LOVE to take her to Yosemite for her first experience camping under the stars and hiking some of the JMT. Fly IND to SMF.

      Thanks Chris!


    • Vicki Johnson says:

      I would love to go New York City! I want to do MOMA and the Guggenheim and of course do some shopping. Thanks for sharing the wealth!

    • Kathleen says:

      To visit my mom in Indianapolis! Thanks for generous offer!

    • Kris says:

      Hi, Chris,

      You aren’t just an inspiration, you give us a chance to make our dreams come true. My choice would be a flight from Denver to Seattle and extend that to British Columbia and Vancouver.

      Thanks, Chris.

    • Matt says:

      Thanks Chris! Love your blog!

      I would fly my sister and her husband (and her newborn who flies free!) down from Philly to Houston to visit. I haven’t seen them in months and they can’t afford tickets.

    • Providence, Rhode Island, + Austin, Texas. I’ve never been to Rhode Island (or North Dakota or Alaska), and going will take me up to 48 states and counting. And though I’ve been to Dallas 482 times (approximate count), I’ve never once made it to Austin. Thank you, Chris!

    • Robert says:

      I would go to Orlando FL. to visit my sister.

    • Katie says:

      I would use the tickets to fly my husband and I see family using the BOI-DEN-MCI routing!

    • Uri says:

      It turns out that almost only Southwest flies direct from RDU to MCO, so to get all five of us to Disney will really be much less expensive with 25000 SW miles…

    • Ashley Coffman says:

      Orlando for our first ever trip to Disney world! πŸ™‚

    • Caroline says:

      With the 50,000 miles I would take my husband from NYC to Springfield/MO. This is where I met my future family for the first time, where we got married and where we were part of adopting Mocha from a shelter. This all happened in July 2009 and we have not been back since. It would be so wonderful to surprise our family over the holidays with a visit. And also to see how Mocha, the lovely tabby cat, is doing.
      Thank you Chris for your generosity and your amazing inspiration.

    • Steve says:

      I will be travelling all around the country this fall and winter for residency interviews. Portland, Seattle, LA, the Bay Area, Salt Lake City, Tucson, Albuquerque, Philadelphia, DC and Chicago all places I hope to be traveling to!

    • Emily says:

      I would use the miles to fly home to Missouri to spend the holidays with my family. Flights from LA aren’t cheap, expecially during an already expensive time of year.

    • Dharyll says:

      Hey Chris,

      Hmm. I think I’d take a trip to New England. It’s the only part of the country I have yet to explore. Would love the opportunity to do so!


    • John King says:

      My wife and I would fly to Panama City and rent a car to drive to Tallahassee to see our first grandchild–a boy! Would love to use them in February to be there for the birth!

    • Zach says:

      I would use the points so my fiance and I could make it home this year for Thanksgiving!

    • rosanna says:

      If I won the miles I would make a pilgrimage to our capitol and request an audience with our lawmakers to draw more attention to military sexual assault and all that can be done to end the problem. The documentary The Invisible War started another movement to end these crimes, but with everything that is going on in the world I fear the cause will again be pushed down the list of priorities.

    • Heck, I’d get myself to the nearest US airspace (Detroit) then use them to fly to Portland for WDS!!

    • Yup, definitely to get myself to Portland next July – just bought my WDS 2014 ticket!

    • Jonathan says:

      I’m so incredibly thrilled to be attending WDS 2014! The last few years I was just kicking myself so hard for not making the effort after being such an attentive reader for so long.

      Also – thank you SO MUCH for telling us about Die Empty. I downloaded it right away and have been hooked. It’s exactly the medicine I was looking for.

      Right now I’m in the midst of re-engineering my life and I’m going to use July 11, 2014 my goal for a complete transformation because… I don’t wanna be the only boring, unremarkable guy there! (: This road can be so lonely sometimes… I’ll be chronicling my progress online and hopefully can connect with some like-minded folks!

    • Jason says:

      I would fly from washington D.C. to Nashville, TN!

    • Jan Bourdo says:

      I hope your feline assistant reads this! My husband and I would go from ATL to STL to visit our 2 daughters. One is married to an Air Force man and one is dating Air Force man stationed at Scott Air Force Base. Thanks for your generosity!

    • katherine says:

      I would love to be able to see my family in MS for a Thanksgiving.

    • Linas Kasparaitis says:

      I would take my wife home to see her dad who’s been having medical issues. So it would be into Jackson,MS. Birmingham, AL. Or New Orleans.

    • Robin says:

      I would split the tickets up (if that’s possible) and use one to fly my mom to see her sister (my aunt) in Seattle and then use the other ticket to fly my daughter home from Florida for a visit. If they can’t be split, then my wife would have to pick a place. πŸ™‚

    • Michelle Dubovsky says:

      I would take my mom to Las Vegas. She has always wanted to go.Her health is gradually deteriorating due to a genetic nerve disease and other complications so I need to take her sooner than later.

    • Beverly Lynn says:

      I am pulling for the Disney trip requests! I would use the miles to fly from Orlando MCO to Cleveland, Ohio to attend a weekend conference of independent business owners. The conference is March 28, 2014 to arrive by 4 pm through March 30, 2014 after 6 pm departure. We could be flexible about times. The hosts of the conference support and serve on the board of directors for the US Dream Academy, a non-profit organization that mentors children of prisoners in the US in over a dozen major cities (including Orlando). I would use the two tickets for my two adult children and pay for my own ticket. The power of association is so important! The mission of ReagansMom.Com is similar to the US Dream Academy – to help those who cannot help themselves – and association with like-minded folks is necessary to learn to think like them. I am so happy with my Adventure Capital course progress that I must admit that I am pulling for the Disney trip folks. By that time my profit increases from the Adventure Capital course corrections should provide funds for our flights. I’ll post some Disney pictures on the ReagansMom.Com Facebook page in the next few days. Go Disney trip folks!!!

    • Hi Chris, I met you at the Problogger conference in Melbourne last year and I would love to be able to attend the WDS 2014. I would fly to San Francisco under my own steam and then take it from there. I am trying to set up rowing camps in the US and Canada for Australian and New Zealanders to visit and as a result being able to donate back to some of the smaller rowing clubs supporting older and adaptive (disabled rowers). Thank you for giving all of us this fantastic opportunity. Kind regards, Kathy Phillips

    • Jackie B. says:

      I’d travel from Atlanta to Oakland with my kids (I’d purchase one ticket)

    • Stacey says:

      I’d love a couple of tickets to Santa Fe for a Fall getaway with the hubby!

    • Kristen says:

      What I’d really like to do is take those miles and give them to people who have a dream to volunteer somewhere or begin a socially conscious enterprise, but no means at the moment to make it happen.

      My online community is full of world changers, idealists, and people who lead with their heart and I know two round trip flights could open up a lot of possibilities for them to explore opportunities to make a positive impact in the world.

      Hell, maybe I’ll even meet up with them and we can do lots of good together…

    • Cathy Shields says:

      I joined the cartel a year ago as I thought it would help me realize my dream to travel. I am still just as clueless about the whole thing. I would take my daughter to one of the south eastern states. Thank you for doing this.

    • I have yet to fly Southwest, and would love the opportunity!

    • Tom Conway says:

      Hi Chris,

      I’m recently divorced living in Tampa FL. At every opportunity I fly to NY to spend time with my two young children who live their with their mother. On an average income this is financially taxing, but quite necessary. So, I would go see my children in NY, who I adore.


    • Jim says:

      I would use it to go to San Juan, Puerto Rico!

    • Tanis S. says:

      I would love the chance to fly from SAN to MCO to take my wife to Disney World! I was recently reassigned for work, so she has been living across the country on the east coast in support of the transition. I can’t think of a better way to thank her than to make one of her dreams come true!

    • Kris McG says:

      My husband and I would travel to one of the Portlands. I have visited Portland, OR briefly, but my husband has never had the pleasure. I keep thinking about Powell’s Book Store and the great restaurants and how much fun we would have. Or we would travel to Portland, ME. I work on the coast of Maine in the summer, but we have never had the chance to experience the rocky coast in the fall or winter. Thanks for the chance to enter!

    • Amy says:

      Thanks for your generous offer to share miles. My husband and I work so we have money to travel. It’s our hobby. And of all our adventures, the grand canyon is our favorite place in the whole world. It ranks over machu picchu, NYC, Uganda, Mumbai, Hawaii. It is mother nature at her finest. We would use these tickets on SouthWest to head to the grand canyon for our 20th wedding anniversary. A hike to the bottom cleanses the soul and reminds us of what’s important in life. What a treat this would be. Thanks for considering. Amy Z

    • Marc says:

      My lovely fiancee would go to New Zealand for our honeymoon!

    • Liz says:

      I quit my job in 2010, and before I could take next steps to live the unconventional life that I had envisioned, my mom was diagnosed with cancer. As her caregiver, I work multiple part-time jobs to pay my bills and also be available for her treatment and care. Since coming home from WDS in July, I have finally been able to identify a way to pursue my passion project without neglecting my personal responsibilities. However, my family responsibilities and financial obligations make it virtually impossible to carve out the uninterrupted time I need to get things off the ground. I would love to take a one-week sabbatical without distractions so that I can tackle the important groundwork necessary to start generating revenue, and ultimately more schedule freedom to better juggle my personal responsibilities. Location-wise, when family matters eventually quiet down, I hope to relocate and am considering Colorado, Oregon, and North Carolina. It would be great to travel to combine a sabbatical with a geographical site-visit and feel what it would be like to live and work in some of those areas. Chris, thank you for this opportunity and for all you do.

    • Sherri says:

      Awesome giveaway Chris! I would definitely go to the City of Roses (As you know, Portland)!! A friend has been telling me that it’s a wonderful city with awesome food and people, and of course a chance to check out WDS would be incredible. While there I would also try to get out to Astoria, a place I’ve been dreaming of seeing since I watched the Goonies as a youngin’!

    • Sherri says:

      Forgot to mention, it would be from Detroit-Portland πŸ™‚

    • Jeff M. says:

      Hey Chris,

      I would use the 50,000 miles to visit states I haven’t been to: SEA -> PHL, or SEA -> ABQ (to check out BrBa sites), or SEA -> ATL.

      Thanks for the opportunity to win these miles Chris.


    • ym says:

      I’d head for the West Coast, a place I’ve been only once in my life and have long wanted to see again. What’s more, I have a book coming out soon, and some places there would like to have me speak on it but can’t afford to bring me all the way from the northeast.
      However this goes, your large spirit is inspiring.

    • I’d like to take my wife to West Palm Beach to see her mother. We have had a challenging year with a family illness that has kept us on the West Coast, and my wife’s regular trips to Florida have been put on hold. Her mother is not getting any younger and so it would be lovely to surprise both of them.

    • JD D says:

      I’d go to Seattle. We live in FL so it’s the opposite side of the country and have a couple old friends we’ve been meaning to visit for awhile!

    • Catherine Cerulli says:

      Chris, I add my gratitude to all the rest for this generous offer. I would give these tickets to my just married son and his wife in Seattle so they could return to the East Coast for the holidays. Even with creating so much of their wedding, it has strained their finances to the point that “home for the holidays” is not possible. It would be the best holiday gift ever for us all.

    • Tessa says:

      I’d fly to New York City with my husband for our first trip ever on an airplane!

      Crazy I know….

    • Brandi says:

      My husband and I would love to visit the breweries in Oregon.

    • Adam says:

      Chris, I would use the points to fly to Santa Fe and visit my uncle. I’ve just recently reconnected with my fathers side of the family and my uncle tells great stories that I can’t get enough of. I want to record them before its too late and they are gone forever. I’ll go even without the points but they would help! thanks.

    • I’ll take my two CA born and raised sons to visit their grandparents in MN. We haven’t been at the farm where I grew up in several years and it’s good to reconnect with roots, family and some authentic bratwurst from my uncle’s meat market. My 18 year old is in his first year of college at Cal Poly SLO (go Mustangs!) so free tix will help the travel budget immensely! Thanks.

    • Philip Raymond says:

      Oh the places we’ll go!

    • I’d hop from MHT to Midway to MSP, to visit with folks in northern MN and WI, where I have some research to do on different cultural understandings of wolves, in Ojibwe and Euro-American communities.

    • Sarah-Ann says:

      First, I would like to say thank you for doing this. It’s awesome.
      I am not sure if I am too late or not, but I wasn’t sure I would enter this.
      Honestly, I am not sure where I would take my husband. But I do know that I would go on a trip as a celebration of our life together over the last 10 years.
      We didn’t have a honeymoon, since we always have had kids around. This is something we both didn’t care about. But over the last 10 years, my husband has been so amazing, that I feel celebrating our life together by going on a trip (it would be our 1st trip without kids) would be the best way to use the tickets.
      Thanks πŸ™‚

    • Thyrone Tommy says:

      This is amazing! One of my best buds is getting married. We’re planning on doing his Bachelor Party during Mardi Gras in New Orleans. I would definitely book our tickets through southwest and fly out of Buffalo. (Toronto is super expensive)

      Also WDS 2014 Tickets! Amaze-Balls. Due to my ridiculous job scheduling I’ve never been able to attend, but I would turn down a Speilberg movie on cats to be there if I won tickets. (maybe not if he’s actually filming cats). No no, I’d show!

    • Kiki Reef says:

      I want the tickets to go visit my 90 year old grandmother with my son at Christmas. I live in LA and she’s in Indiana.

    • Carrie says:

      I’m a young professional and I recently got a job placement in southern Spain at a bilingual primary school teaching English and North American culture. It’s an awesome position and opportunity, but they don’t pay for my travel to get there, unfortunately. Once I get my visa, I’ll have to purchase a last minute flight from Minneapolis, and having 50,000 flight points would help me more than I can express!

    • Liza Kane says:

      Thanks for the giveaway! I would love to go to Orlando–>The Wizarding World of Harry Potter has been on my wishlist for years! ^_^

    • Zander Galloway says:

      I would without a doubt go to Boulder. After WDS this year, I was inspired to change my life and take my business to the next level. Coming from a geographic area where online entrepreneurs are few and far between, I know that I have to change my environment to take the next big step in my journey. I crave being around like-minded people. I’ve got a few places in mind, and Boulder is on the shortlist of places to explore.

      You helped change my life back in July, now I’m asking you to help me continue on this path.

    • Karen says:

      When we promised our nephew a trip for his 16th birthday, we were still married. Now that we’re separated, I can’t afford the trip to NYC that my nephew wants–and that I’d love to take him on. This would be a wonderful treat for a great kid, who has had more crap rain down on him over the past year than a kid should have to put up with.

      Thanks for being so generous! I’ve been travel hacking myself, thanks to you. Planning a trip to Italy with my sister–who has a nearly free place to stay–and a different nephew for next summer.

    • Vicki Hill says:

      Sacramento & Portland…self-guided BrEw-ToUrs! (I’d love to say thanks! & buy you a beer, if you’re at home in Portland.)

    • Andrew says:

      I think that the best place I could go would be to Columbus to visit family.

    • Kirsten says:

      I would take the tickets and go to Charleston with my husband and my camera. I was there once over ten years ago and it inspired my first art show. I would love to find the moments of grace that I found there the first time to inspire a new chapter in my photography and art.

    • Britt Ide says:

      San Diego! Beach & friend time for me; take my 6 year old to Sea World for his birthday; and do some meetings for my business. There is nothing like the calming effect of watching the waves and listening to the surf. I love the mountains but I need my fix of ocean. Thanks

    • Jonathan says:

      I’d use the tickets to just go somewhere, anywhere to get a change of scenery from my teaching job (during a vacation of course).

    • Brenden says:

      I’d use the tickets to visit my daughters. πŸ™‚

    • Katie says:

      I’d fly to Seattle to visit my best friend. I miss her a lot! (Thanks, Chris!)

    • Brian Webb says:

      You’re too kind! I’d fly to Portland to visit my brother. We live on opposite sides of the country now and don’t see each other often enough. Oh, and I also want a Voodoo Donut treat.

    • Patrick says:

      This would be awesome. I would take out new baby to TPA. Thanks for sharing, Chris!

    • Adele says:

      I would go to Detroit. Have you seen “Detropia”? Would love to photograph, blog about the journey and contribute art to the community.

    • shadygrove says:

      We’d head to MN, to see family!

    • Matt says:

      I would take my girlfriend on our latest planned trip. NYC>SEATTLE>PORTLAND>NYC. We’d go on a brewery tour and see the National Forests all over the Pacific NW. πŸ™‚

    • Michelle Taylor says:

      I love flying souuthwest – to hang with family & friends on the east & west coast. I love the ‘old’ southwest, but am not liking how they are starting to follow the practices of the other large airlines & not truly value their frequent flyers. Thanks for the contest!

    • I am in the middle of a long tour of South America with my 2 little kids- ages 3 and 5, and my little dog Hippie. I would use the miles to help us get to Buenas Aires at the end of 2014 where we plan to take a tour of Antarctica! πŸ™‚

    • Corey says:

      I’m ready to go back home to San Antonio.

    • John Graham says:

      Definitely Thailand. Tropical, delicious food, far away. I’ve never been to an international destination. Only been inside the US. I deserve a taste of paradise!

    • Andy P says:

      Chris, enjoy your blog. Just bought Die Empty. Looking forward to WDS next year as well!

    • Jonathan says:

      Washing DC

    • Andres P. says:

      Never been off the east coast of the United States. I would most likely visit Beverly Hills/ LA. I hear In-N-Out Burger is worth flying across the country.

    • Ryan Fleming says:

      Like Oscar Wilde once said- ‘Resist everything but temptation”.

      You fire me up Chris. Although I have never physically met you- totally admire your work and outlook on life. You have set some ambitious goals my friend- but don’t worry I am right behind you. Love to use those miles to revisit family back in Melbourne, Australia. ANOC inspired to live abroad this past year- but had to come home suddenly to California.

      Anyways- keep at it-


      Long Beach, CA (the LBC)

      P.S. Any idea when Southwest or Chase start offering miles with Virgin Galactic? πŸ˜‰

    • Ingrid Lembach says:

      Portland, OR. I’ve always wanted to visit there, and I can see relatives I haven’t seen in years. Pick me!

    • If selected I will fly to new york to photograph places I have yet to see then fly to Oklahoma visit my family and use the remainder to see other states I haven’t visited.

    • Chris g. says:

      thanks for the generosity! I’d love go go to New York because I’ve never been. I’d like to experience all the diversity there from food and drinks to the cultural events. cheers!

    • Jennifer Underwood says:

      Also, since reading your book two weeks ago I’ve quit my job and started to change everything about my life. If I got the miles, I’d take my daughter on a trip as a first step in my desire to show her the world doing volunteer work and studying history. She’s 6, and my sincere hope is to be in a place within two years where I can homeschool her and travel extensively on humanitarian missions.

    • Courtney says:

      I would fly to San Francisco via Southwest, because Yosemitebear (the Double Rainbow guy) sent me a message about WWOOFing on his farm, but alas, I am a grad student, flying to SFO es muy caro, but this would be A DREAM. Actually, two, since I’ve always wanted to WWOOF, and I share a mutual love for rainbows (I was a double rainbow for Halloween a couple years ago).

    • Margaret says:

      Hi Chris!

      I would fly to San Francisco to do a tour of the redwoods and a wine tasting in Napa and Sonoma Valley. One more thing off the bucket list πŸ™‚

    • Gil Friend says:

      Probably FLL…depending on timing. Maybe San Diego. Let’s discuss it after I win. πŸ˜‰

    • Steven W says:

      I’m moving to Oregon this month so I’d use the opportunity to fly back to Minneapolis to see friends and family.

    • Leslie Strom says:

      What a fun offer of miles! I have two vexing genealogy gaps I’m trying to research my way through. I’d use one ticket for Salt Lake City and the LDS archives, and the other later for Boston where most of my dead relatives are, and the New England Historical and Genealogical Society has a magic vault with some un-digitized original stuff in it. The collection at SLC is gigantic and rather exhausting, and Boston would entail a lot of driving, so definitely two separate trips. I love both places in winter and living history is such fun!

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