Giveaway: Win 25,000 American Airlines Miles

Every Friday is giveaway day. Comment to win!


We wanted to do something extra special for this week’s giveaway… by offering 25,000 miles that can be used for a round-trip ticket with American Airlines!

See a new place, visit an old friend, or check out that wax museum you’ve always dreamed of. The possibilities are endless! (Well, they’re subject to availability—but still, there are a lot of possibilities.)

Share with us which exciting destination you’ll go if you win.

What you need to know:

  • 25,000 American Airlines miles are valid for a round-trip Economy class flight anywhere in North America. You can also use them for an intra-Europe flight (on partner airlines British Airways or Iberia, for example), and intra-Asia flight (on partners Cathay Pacific or Japan Airlines, for example), or many other options. See the AA awards chart to learn more.
  • These miles aren’t transferable to a friend, but you can book the ticket in whoever’s name you like (in other words, if you don’t want to use them yourself, you can use them for someone else)
  • This giveaway is available to readers worldwide. Anyone can win!
  • Our cats and biased judges will pick someone on Sunday night at 6pm PST

Enter this week’s giveaway by posting a comment, then check back on Sunday night. We’ll announce the winner and send them the prize!

Update: this week’s giveaway is extended one day. We’ll announce the winner on Monday night!

Update: Comments are now closed. Congrats to Rachel Medlock, selected by cats and a random number generator to win the 25,000 American Airline miles! Everyone else, thanks for entering. We’ll have another giveaway next week.


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  • Daniel Boga says:

    Hey Chris! My name is Daniel, and I’m a Brazilian fine-art photographer. I would love to win this points to do my trip to the Iceland and Europe, documenting all the beautiful landscapes that I’ll see at those great places!

  • Stephanie says:

    My quest is to learn and teach others about traveling for the first time abroad! Points are always useful in getting me around to learn more and help others. 🙂 Thanks for all you do!

  • Victoria says:

    Hi there! I’d love to win the miles so I could fly home and see my family! Fingers crossed 🙂

  • Patricia says:

    Exciting! In 1993, I went with 2 friends to Chichen Itza, Mexico – reluctantly. After a tour guide, Reuben (still remember his name) spent 2 hours with us, I was transformed by the experience. At the end of the tour, we were sitting in the shade and I felt like I was a different person. Here’s to the idea of saying yes when you aren’t fully inclined!

    If I won 25,000 points with AA, I would go to Guatemala and see those Maya inscriptions up close. I would like to share what I learn through articles and a presentation at the local library. I think it would be a great addition, too, to any schools. I would check it out!

  • SL says:

    I would love to use the miles to celebrate my anniversary in Paris with my boyfriend. Thanks Chris! You’re the reason why I got into the points and miles game after watching your CreativeLive course! You rock!!!

  • Agustin says:

    Is there anything better than having the chance to work as a motion graphic designer and animator from any country in the world? Would love to win this.

  • Kevin says:

    With another 25,000 miles, I think I’d finally make it to Hawaii.

  • Daryl Conner says:

    If I won I would visit Chicago. See some friends and see the city. I live in Texas and have been in the South all my life. Now I would like to see more of America. It would be such a lovely gift from the universe and God. Life can be so wonderful. I am sending blessings to all.

  • Kenn says:

    Just dropped a bunch of points on business class for two to Panama so I need to build up the stockpile again (I’ve been hovering just shy of 1,000,000 but haven’t been able to cross that threshold).

  • Shaozhi says:

    Wow! After spending a year and a half in Asia, I arrived in Los Angeles a few days ago. If I won, I would love to visit Vancouver, Canada (even though I’m a Canadian, I’ve never been to Vancouver!!)

  • Jared says:

    This would put my family of 4 one seat closer to our next trip.

  • Allen says:

    Would love to visit my sister in Shanghai next year!

  • Paola says:

    I’m not sure I could use the miles myself because I live in Europe…though it would be great to fly to Iceland (one of my biggest dreams…)! Fingers crossed!

  • Stephanie says:

    Would love to see the Badlands this year!

  • Ismael says:

    Great giveaway. Love your blog. This would be perfect for a quick weekend getaway to Europe during off peak.

  • Rick says:

    San Diego to Dublin. Would love see the grass-fed cows making my Kerrygold butter during the day and hang out in some Irish pubs in the evening.

  • David says:

    I would love to visit Antartica!

  • Maggie says:

    Hey Chris!
    This morning I stopped by the Chinese consulate to pick up my first visa, for my first ever trip abroad – and on the way out they told me “It’s for multiple entries, and is good for one year.”
    I’ve been so focused on my upcoming trip I hadn’t even thought: where will my next trip be?
    I’m so excited to start traveling the world, thanks for the confidence!

    (Loved seeing you here for HoP release in Brooklyn!)

  • Susan M Hall says:

    Jacmel, Haiti for the “Let’s Go Haiti” half marathon January 4, 2015.

  • Jonathan Ytreberg says:

    Thinking of taking the kids to Disney next year, this would be perfect to take care of one ticket!

  • Jeff says:

    Would love to go to NY if I win.

  • Cata says:

    May the cat gods be in my favour

  • Christine says:

    I would love to win the miles!
    It would support my plans of taking a sabbatical

  • Matt says:

    Houston (not exactly exciting, I realize, lol…)

  • Lyndsay says:

    Pick me! Pick me! {raises hand enthusiastically like a first grader who has to potty}

    Thanks for your writing!

  • JamesP says:

    25,000 AA miles would be enough for American’s great off-peak one-way award flight to Japan . Thanks for the contest! Meow.

  • Steve says:

    Best of luck…. to me! 😀

  • Christian E. says:

    I would love to go to Istanbul and finally see my students face-to-face 🙂

  • Marc says:

    Would love to get these 25000 miles.

    Been living in NYC for 5 years, and now living in Madrid. I have some miles accumulated, but not enough to get my dear wife and 2 little girls over there and visit some friends not seen in a long time…

    or redeem the miles to get my wife’s family to visit us from Argentina.

    keep on the good work, the world needs people like you.

  • Nick says:

    a Haiku for your giveaway consideration:

    “Free View” by Nick Macek (thats me)

    the view from the clouds;
    beautiful, but made sweeter
    with free AA miles

    thank you.

  • Dr. David Powers says:

    Hey Chris! This is Dave. I’d be using the miles to jumpstart one of my quests that you inspired.

  • Jason says:

    Good timing! My fiancée and I are planning our honeymoon right now (wedding is in May). Thinking about Aruba but still deciding. This would be a prefect wedding gift 🙂

  • Barry Belford says:

    Today is the 1 year anniversary of living my life to the fullest, of realizing I do not have to do this journey alone and that it is more fun when we do it together with others. Today I can say that I am LivingWIDE and pursuing happiness, not for others but for myself. My quest has only just begun, but it is the journey of my life.

  • pep says:

    I would like to go to visit the Natural History museum in London with my 4 year old twins. They like dinosaurus a lot and they would love to see them in the museum.

  • Bobbi says:

    I would use these miles to go to South America where I can brush up on mi español.

  • Diane says:

    If I won $25,000, I would take my Mom somewhere splendid to celebrate her 79 birthday. She keeps complaining that she has taken her last trip…..Take away my guilt!

  • Jeff Skipper says:

    I’m allergic to most Cats, but I hope they don’t hold it against me… I’m building my AA balance and would love to use these miles to create a great trip for the Mrs’ and I.

  • Tasha says:

    A trip back to Seattle would be great! Are using it to go to Mexico … Crosses fingers!

  • Meghan says:

    Although perhaps not as exciting as some of the other destinations, I would love to use these miles to visit family in Florida. My family is so spread out and it’s tough to spend the money to fly across country. Thanks for the opportunity!

  • Jake says:

    Hi Chris! This would be awesome for my wife and I to get the chance to see more of the world!

  • Anne B. says:

    I just finished reading your newest book and I am totally captivated by the thought of going on an Epic Quest of Awesome (makes me smile and chuckle every time I think of being on an Epic Quest of Awesome!! . Winning air-mile points would be an excellent kickstart to an Epic Quest of Awesome – oooooh, I could use the points to fly to the next WDS in Portland – now that would be Awesome!!! TTFN 🙂

  • Elizabeth says:

    I am going to Ontario to visit my Aunt. Winning these airmiles would make it so much easier. Your generosity is beyound fabulous.

  • Zeenat Patrawala says:

    I am running to fund Kids!! I would love to do a second race and take one of these fabulous young runners with me

  • Cassie says:

    This would be so great!

  • Aaron Ramirez says:

    I would use everyone of these miles, to fly as far South as possible!

  • Andrew says:

    Would love 25k worth of miles. Have just gotten into the mileage community, and am trying to build up my points toward a trip to Portland (hear it’s amaz zing) or may try to go big on the first trip and do business/first class to Europe to visit some family.

    Oh and I love cats.

  • Tim Conner says:

    Definitely would use the miles to travel back to Chicago to visit my grandma and see where I grew up. Windy City no doubt!

  • Chase says:

    Good seeing you in Miami, Chris!

  • Brian says:

    Would love to go to Panama to see the canal.

  • Andy says:

    I am hoping to take my wife on an anniversary trip to Hawaii. Would love to have the points to make this happen. Thanks!

  • Ryan Tanner says:

    I’m Ryan, I work at a startup that lets me work remotely from anywhere in the world. Mostly I work from Colorado but I’m about to head to Tokyo and Hong Kong for a bit and then I’ll be working all of February from Vietnam. These points would definitely make it easier to take more trips like that.

  • Krista Soltis says:

    I would love to see my family in Michigan again over the holidays, but with a bunch of unexpected costs recently arising, I haven’t been able to commit to the trip from Florida. Over the past few weeks, my 1-year old cat has been suffering from a raging bladder infection. He has been to the vet six times already, endured 5 days of being catheterized, and countless antibiotic, steroid, and valium shots. Needless to say, I did not see this coming and didn’t realize the potential for thousands of dollars in vet bills and the fact that pet insurance does not cover what is now a pre-existing condition. My baby Gerard is in a lot of pain but still trying to make the best of it. He loves playing fetch and drinking water from unsuspecting people’s glasses.

  • Chrissy says:

    Wowzerz. This will be one lucky person. Let it be me! Please and thank you.

  • Tanya says:

    Hi Chris!

    I’m the illustrator and writer of my project: IllustrArticles – illustrated articles about important stuff. This would be an amazing opportunity to complete one of my goals: To visit New York City, trek around there, and to report on all the important stuff.

    Thank you!

  • Peter Gregg says:

    Hey Chris. Great giveaway. I would use the 25k on top of the miles I already have to take my family to Europe. Both grandparents ashes are spread there and I am first born US. We havent taken a vacation in 8 years due to the economy and work and this would facilitate the dream of “going home”.

  • Audrey says:

    I’d go visit friends!!! I have a new baby, so my trip would turn into a 2 for 1 deal since he can come along in my lap. 🙂

  • Tim says:

    With the 25,000 miles, I would fly to Seattle and then spend time traveling down the West Coast on Amtrak’s Coast Starlight, stopping at multiple cities along the way, then fly home from Los Angeles.

  • Alice says:

    That would make for a lovely weekend away with my special someone.

  • Zander says:

    Hey Chris, I’d be going to Chile with those miles. I’ve never been to South America, and Patagonia has been on my bucket list for a while. My next trip has been a long time coming, and these miles would go a long way towards getting me there.

  • David Phelps says:

    Hey Chris. I would take my wife back to Key West, we were married there on New Years Eve.

  • Sarah M says:

    yes, please!!! I would take the first flight to Portland, and buy my best friend a ticket to meet me 🙂
    Sarah M

  • Clare says:

    Got the travel bug over here 😉

  • Kathy Gould says:

    Great prize. I could use it to visit family!

  • Jessica says:

    I would love to win a ticket to Lusaka, Zambia (where I live) for my best friend, Rachel. She hasn’t gotten to come visit me since I moved there in 2010, and I would love to show her my life there.

  • Dave says:

    Hmm, maybe the caribbean for some epic scuba diving. You cant really beat warm, clear water IMO.

  • Pauline says:

    I’d love to use those Miles to go to Turkey! It’s been calling my name for a while now and I should visit sooner than later 🙂

  • Tony R. says:

    An extra 25,000 AA miles would contribute to the stock pile I’m building for my next trip, French Polynesia. May the odds be in my favor.

    *Fingers crossed – looks up to the cat gods*

  • Rachel Medlock says:

    I don’t want to travel – I need to travel. My insistence upon constantly pushing myself beyond the comfort zone is magnified every time I step onto a plane. I refuse to settle for the version of “normal” that I was raised to be (housewife, 4+ kids, lots of Bibles) or the version that I am fed constantly (career woman, dutiful but driven wife, Midwestern perfection). Instead, I tell people that sunshine and beer are my religion, and that experiencing new things is my passion – all of which is true. There are probably a lot of people that deserve the miles as much or more than I do, but every good thing in my life has been a combination of hard work, luck, and someone taking a risk on me – so what do I have to lose?

    Have a lovely day,

  • Luis Mollinedo says:

    I would use the miles for traveling to Asia, I want to learn about these cultures and it’s development of business in the world, best regards from Guatemala 🙂

  • Nicole says:

    I’d take the honeymoon my husband and I never took. It’s been five years and our four year old is still in the bed with us! We NEED a honeymoon. You feel me?!

  • Kat Hester says:

    Dear Chris,

    Traveling is in my blood from living in Asia as a child.
    I haven’t been out if this country in so long, that sometimes I wonder if I ever DID live anywhere else!!

    Adulthood, parenthood and tuitionhood greatly reduced my ‘wants’, like traveling to other lands or taking trips within this amazing country.

    I’m interested in seeing so many more geographical sites…too many to list. The world is waiting to be ‘connected’ by US. So, points for traveling would be euphoric on
    many levels.

    Keep up YOUR quest!!!
    Kat ;”)

  • Kat says:

    So hard to choose! In the words of Susan Sontag, “I haven’t been everywhere, but it’s on my list.”

  • Daisy says:

    Hi Chris, I’ve spent my morning watching your interviews on Youtube started with the one with Marie Forleo on discussing about your book which I already ordered! Can’t wait to read it. You have been a great inspiration and I will continue following my dreams and in my quest for a more fullfilled life that of course includes lots of travel. I would use the mile points to visit a friend I met in Madrid in Merida, Yucatan Mexico! 🙂

  • Jake Peters says:

    25,000 miles would help towards my partner and I starting to live as digital nomads. First stop Argentina!

  • Bonnie E. says:

    Great giveaway! If I won, I would either visit my family in Asia or go down to Mexico for a scuba trip 🙂


    I live in Ireland & would welcome Jeff (above) to our village so he can wander the fields with the cows & eat real spuds (potatoes) and homemade bread with his Kerrygold! Apart from that, I wouldn’t mind a trip to the States!

  • Katrina says:

    If I won, I’d go to the Maldives!


    Sorry – that should have been Rick (not that Jeff wouldn’t be welcome)!

  • Molly P says:

    I’m getting married in a week, so I’d use 25,000 to take my new hubby on a nice honeymoon this winter. Maybe Barbados?

  • Joseph says:

    I’d love to go to Korea using AA miles. Just need 50,000 more points for my wife as well!

  • Amelia says:

    I would love to win some points and visit my sister in NYC!

  • Morgan says:

    Umm yes please! I would use these points and my own collection of points to fly my boyfriend and I to New York for a long weekend of mischievery.

  • Shirley Braden says:

    We’re working on our bucket list for travel all the time so these miles would be a great help! Thanks for the giveaway!


  • diane says:

    Wow, Chris! 25k miles kicks “If I coulda, shoulda, woulda” right out the ballpark. Its time for more travel and less excuses. Thanks for the opportunity.

  • Steve Evans says:

    We’re working on our bucket list and would love to fly instead of drive.

  • Daniel says:

    I would love to use these for a flight to Colorado.

  • Ivana says:

    Hi cats and judges!

    I’ve started documenting my travels recently as well as discovered my love for diving. I would love to visit Miami or Key Largo to further both experiences.


    Ivana @

  • Benjamin Palmer says:

    Hi! American working/living in Kuwait – would love to use the miles for taking a holiday around Southeast Asia!

  • Kendra Kinnison says:

    Chris –

    This is awesome! I’d love to win so that I can take my 87 year old grandmother to San Francisco. That’s one place she’s never been and that she’s actually willing to travel for. She also won’t let me pay for it, so this would surely make it happen.

    She hasn’t been on a west coast trip since my grandfather passed away in ’91, and I’d love to get in another adventure to rekindle those memories.

  • Stephanie says:

    Would love to go on a photography trip – anywhere!

  • Jessica T says:

    Been itching to fly back to Hong Kong to visit family and friends, but would love to stop by Japan first 🙂 Last time I was in Tokyo was over 20 years ago!

  • Jenn says:

    I’m praying to the cat gods! I would SO love to win these miles and plan a trip from Germany to… Scotland? Spain? I didn’t have a chance to leave the country this year. Not yet anyway 🙂

  • Andrew Elsass says:

    Never left the States (yet), so I first want to go someplace pretty ‘out there’ that will feel like bizarro world to me…Tokyo!

  • anne says:

    would love to use these points towards a return trip to asia!

  • Kyla H says:

    These points would certainly help me book my first-ever trip outside of the U.S. to Europe next year (hopefully a backpacking trip through 5 or more cities!)

  • Andrew Crocker says:

    I will use the points to travel back to my childhood home of Colorado to see my first real snowstorm in years!

  • Lindsey says:

    I’m in a long distance relationship. Help some star-crossed, geographically-challenged lovers out!

  • ALAIN C says:

    I want the miles! All 25,000 of them! 😉

  • Julien says:

    I’m currently reading The Happiness of pursuit… I’m about to quit my job and start a new adventure. Thoses miles would help but even if I don’t get them. I’m still going to do it anyway.

  • Tracey says:

    It’s been a long time since I had the luxury of traveling abroad…My list is long but I think I’d either go to Costa Rica or to Europe.. Its been a long time since I walked the beautiful cobblestone streets and felt carefree. I’m a photographer and the most exhilarating time for me is traveling and seeing the world in a new way…
    I love your blog Chris and the thought that I too can be a frequent traveler makes me happy… I’m starting to rack up those miles so 25,000 more sure would help!
    Thanks for all the great info!

  • Matt says:

    I’d use the miles to visit my ailing uncle.

  • Alex says:

    I hope I win!

  • Francesco says:

    Awesome! The best giveaway ever! I’d like to go to Paris!! 😀

  • Ruthie Rochman says:

    Hi Chris,

    Should I be the lucky winner, I would return to Honduras to work again on a medical mission with my cousin who runs medical clinics (among other programs) that help the rural poor. I went in 2007 the first time, and would love the opportunity to be able to help out again!

  • Andrew says:

    Looking forward to lots and lots of miles. I also think the new comment box should appear at the top of the current comments, not the bottom of the webpage…but hope I still win.

  • John Pedroza says:

    Wish this contest was one week earlier since I am on my way to Belize on AA tomorrow, but still happy for the contest and a chance to win. I want to go to Europe.

  • Dave Grant says:

    Hey Chris, both my wife and I are on disability pensions and we are caring for our youngest daughter who is 31 and been disabled since the age of 22. My wife just turned 60 on September 18th and I would see the miles to send her to Ohio to see our other daughter and grandson. She had to forfeit a ticket recently because of the hospitalization of our youngest. This would be a nice birthday present.

  • Irene says:

    Dear Chris,

    My husband and I would love to take our just-turned-1 year-old baby daughter (who was a miracle baby) and her 8 year-old brother to go see their 94 year-old great-grandmother who lives alone in Upstate New York (we live in California). Airfare is not inexpensive for a family of four, so we would greatly appreciate any help just to visit aging relatives.

    Thank you for your blog and for the great ideas I’ve read and learned.


  • Heather says:

    Great meeting you last night, Chris. You are just as kind as I imagined. Keep spreading the good word. Looking forward to WDS!

  • Emily says:

    My cousin is getting married outside of D.C. and there’s a call out for the whole family to gather for a once-in-a-decade reunion (we’re spread all over the place and can very rarely meet up). It would be so lovely to win these miles; I’d be able to confirm my participation in the festivities (it’s currently on a wait-and-see-with-fingers-crossed status).

    And if the miles go to some other lucky winner, I hope they make a special moment possible for them too.

  • Lillian Duggan says:

    Hi, Chris. Saving miles for a family trip to Europe, but these could make it possible for me to use my golden ticket and go to WDS next year. Thanks for doing this!

  • Claire says:

    Two years ago I started my own business after reading back to back the Art of Non conformity and the $100 startup. It so resonated, I started the week after finishing reading the second book.
    It’s been quite ride with ups and downs, but people like you have continued to inspire me; reading your blog (now on a daily basis!) is one of the things that made me hang tight.

    I’m turning 30 this winter, and as I now have the freedom to manage my time the way I want to, I would like to take an educational and memory trip to visit the concentration camps of Auschwitz Birkenau. 25,000 miles would really help 🙂

  • Jon Doench says:

    As the tired parents of 20 month old twins, I would use these points to take my wife on an ocean kayak trip in BC Canada. We love to travel and can’t wait to start again! (Maybe we will take the kids with us! )

  • Jenny says:

    Very cool — I’d use these miles to fly my daughter out from Texas to Seattle to go to Sakura-Con, the PNW’s major anime convention. She’s way into cosplay & I know she’d have a great time.

  • Ryan Sitzman says:

    Hello! I’d use the miles to travel with our baby from our home in Costa Rica to visit family in Colorado. It’d not be enough for a round-trip from Central America for 3 people, but it would certainly help.

    Anyhow, there are lots of other great answers, too. Thanks for the website and all the great posts!

  • Debbie Flowers says:

    30th anniversary trip!!

  • CB says:

    I’ll go to my college roommates’ bachelor party in Asheville, NC. So much nature and beer!

  • Michael S. Armentrout says:

    i would use the miles to head back to New Orleans and reconnect with high school friends.

  • Nancy says:

    I’d use them to book the London/Frankfurt return portion of my 3-month European quest next Spring!

  • Daria says:

    I would take my partner and go to Madagascar to explore its unique nature and culture!

  • Leslie Lynch-Wilson says:

    My #1 priority is to meet cousins my Irish cousins, still in Ireland, that descend from my great-grandmother. I would use these points to either go to Ireland to meet them, a goal, or if they come to the US this November as they often do, then I’d fly east to PA to meet them. My great-grandmother had two brothers who never left Ireland. I have connected online with some of these cousins but would like to go to Ireland to meet them as well as see Dungarvan, County Waterford, where my paternal grandparents came from to the USA settling in Philadelphia, PA.

  • Dare says:

    I hope that cat loves me! I would go to either Savannah or Portland or Austin – or maybe all 3?

  • thomas says:

    I would like to take my wife on a baby moon as she is 16 week pregnant!! PICK ME!!


  • Paul Latta says:

    In the mid eighties I saw a band called The Del Fuegos open up for The Outfield. Great bands both and a wonderful show. Ever since seeing the Del Fuegos, I’ve had a perverse desire to visit Tierra Del Fuego. Outside of Antartica it is a place that is literally “the end of the Earth.” Winning the gift of 25,000 miles would get me closer to making this dream a reality.

    Why would I want to go to Tierra Del Fuego? Well, why not?

    Thanks for all you do.


  • Tracey says:

    Wow, the opportunity to travel this year would be amazing…My list is long but to be able to walk the cobblestone streets of some faraway land would be exhilarating. I’m a photographer and I’m most in my bliss when traveling and photographing…
    I love your Blog Chris. Thanks for all the great info and the opportunity to win this amazing prize… Good luck on the book tour!

  • Alex Luna says:

    Is this just because today I started to plan a round the world trip? 😉

  • Tracey says:

    It would be so exhilarating to be able to walk the cobblestone streets in Europe or explore the jungles of Costa Rica…the list is long and my travel dreams are many…
    Thanks Chris for the great blog and all the wonderful info! Good Luck on the book tour!

  • Asa says:

    Nice! I could use the miles, especially since I have a bunch of USAir miles and the two will be combining mileage programs next year!

  • Harish Krishnamoorthi says:

    Hi Chris,

    My name is Harish and I am a regular reader of your blogs and have listened to you talk at one of Ramit’s programs. I am a travel fanatic. I would be thrilled to win this giveaway just to accompany you on one of your upcoming trips. That would be like a dream come true.

    – Harish

  • Brian Judd says:

    Hey Chris! Love the new book! By far the most simply clever book title I’ve seen. I would love to take my wife to see the cherry trees blossom in DC, or better still, the Rose Festival in Portland.

  • Dayna says:

    I would love to win! My last trip was 4 years ago and I’d love to go somewhere again. I just bought your newest book and it has definitely awoken that travel bug that lives in me. 🙂

  • Aaron M says:

    Thanks for the opportunity to enter this giveaway! I’d use the points to take my girlfriend to Yosemite to propose to her!!!

  • Shannon says:

    I’d love to win these and go visit my family in Phoenix!

  • Tracy Wallace says:

    I’d love to win and splurge on a trip to an art retreat on the East Coast!

  • Rachel Jobson says:

    I’m in Ottawa, and I’d love to use the miles to visit my best friend out west in Seattle!

  • Helene says:

    Hi Chris, cool giveaway! I would use the trip to give a big tour of livingroom-concerts of art songs!

  • Chae says:

    I’d love to travel to Washington DC to let my mom hang out with her now granddaughter!

  • Eric Zimmer says:

    I’ll use the miles to come see you and do an in person interview at WDS. Lot’s of interviews at WDS.

  • Brian says:

    Hi Chris! I’m an aspiring singer-songwriter and one of my dreams is to play my songs at the Mucky Duck Club in Houston, TX, where many of Texas’ finest singer-songwriters gather. I have an insane desire get on that stage and be humbled by the music gods—I have a date set in mind to be able to do this: November 17, 2014. YIKES!!!!

    With the 25,000 miles I would travel to Houston to:
    – Spend an extended weekend with my dad, in my hometown of Liberty, TX
    – See my favorite band in concert: The Tedeschi Trucks Band
    – See my dad’s favorite singer-songwriter in concert: Ray Wylie Hubbard
    – Perform 3 songs at the Open-Mic at the Mucky Duck, for my dad and his songwriter friends

    My biggest impediment at this point is airfare, prices from my city (Memphis) to Houston have skyrocketed. I only get to see my dad once or twice a year so winning something like this would be an amazing thing for both my dad and myself. Thanks for your consideration!

  • Brandi says:

    Hello Chris! First I’d like to say I received your new book “The Happiness of Pursuit,” in the mail yesterday and I love it! If there’s one thing I learned from reading the first 50 pages, it’s that crazy ideas are a starting point toward achieving one’s dreams. And what’s crazier than thinking I could actually win anything? Let alone 25,000 miles toward a trip! But, here goes…

    With the miles, I’d go to my brother’s wedding in Hawaii this fall. My entire family is going (even my nephew who’s just turning one). Unfortunately, when flights were ridiculously low this summer, I was out of a job and not able to afford a few hundred dollars for the cost of a ticket. I’ve since signed on to a couple of wonderful writing contracts, but am still getting caught up to my months of unemployment, and as you know flight prices have risen. It would mean the world to me, my family, and even more so to my brother, to attend this wedding.

    By the way, my quest is to have reached 100,000 miles on American Airlines by the end of 2015, and I’m not even sure how it’s done. Crazy idea, I know! 😉

  • Emil Kiehne says:

    Chris, I recently heard about you by listening to your interview on the Tom Woods show. If I were to win, I’d use these miles (along with others) to take my wife and kids to Rome.

  • Carol Saha says:

    Pittsburgh, PA to see my sweetheart’s parents. Would possibly buy a ticket so he could go too. Ha!

  • Kami says:

    OK here’s the thing. I’ve just read “The road to Sata” and got inspired by Alan Booth who has walked the whole Japan from south to north. Its been my dream to do it since. But i keep postponing it because of many silly reasons.
    Now, if i win this, i will fly to JAPAN and WALK the whole country through, just like Mr Booth. Then i will write about it too. You will hear about my progress as i walk along, so you know I’m not bullshitting.
    No more excuses. So, is it a deal? 🙂 Let’s do it!

  • Constance Spear says:

    I would go to the land of my ancestors – Denmark. Then I would travel to Norway, where the ashes of my sister were scattered by her husband.

  • Jocelin says:

    I love AA airlines and I have a frequent flyer account with them and I have been diligently collecting miles, so these would help me out so much! I’ve been learning and practicing Spanish to pursue my dream of visiting Costa Rica one day! I want to save baby tortugas from extinction by assisting them in getting safety to the ocean after birth.

  • Devlin says:

    I could use these to visit my family back in Chicago for the holidays! I haven’t been back since I started my expat journey into Mexico back in June ’13.

  • Carol says:

    I live in DC and my best friend just moved away, so I’d use the miles to go visit her in Las Vegas. That would make me happy, which, in turn, would make my three cats happy. 🙂

  • Lucha Kutton says:

    I want to win the miles because I’m saving up for a RTW ticket (on miles!)

  • Margaret Smith says:

    25K miles on American would get me from Denver to Fargo and back, which would be really cool since North Dakota is the only state I’ve never been to. Of course, it would also get me to New Orleans – my family passed through Louisiana when I was 7, but I don’t actually remember anything about that state, so won’t really feel that I have visited every state until I get there as an adult. Then there are all the places I need to visit to continue my family history research. So many choices!

  • Marc says:

    I would go to the airport and buy the next ticket to anywhere

  • Mermaid Rose says:

    You gifted me your amazing new book, The Happiness of Pursuit, and after relishing every page, I gave it to my lawyer who is about your age. It brought me so much joy, which I just had to share. I can’t travel right now, but I would give those miles to my nephew who’s gonna graduate next year and going straight to work–no break. I want him to take a trip before he ties his life to a desk. He’s going to USC.
    Thank you for the book Chris. It’s got me thinking big thoughts & little ones–like I’m hosting couch surfers once again in my house. If I can’t travel (right now), might as well support those that can.

  • H2 says:

    I would hook up a friend to come visit me!

  • Barbara says:

    I need … no, I mean, I NEED … wait, what I really mean to say is, I NEEEEEEEEDD these 25K AA miles! I’ve always been a gypsy, at heart, but physically stuck in the middle of Oklahoma. My soul really, really needs to travel, and at nearly 53 I’m more than ready to get started. California next week … Italy and Greece next year (I hope) … and who knows from there?

  • Amy says:

    I’d take a trip to New York – it’s my 30th birthday in December and I’d love to experience the holiday season in America!

  • Adelina says:

    I’d love to go to New Orleans! I haven’t been to the south and everyone raves about the fabulous food options. I like food and exploring new cuisines so its the perfect place to visit.

  • Jenny Renegar says:

    Dear cats and biased judges,

    Please pick me <3 I am a new digital nomad and travel hacker. I am a big fan of Chris Guillebeau *and* cats of all kinds! Thanks for all that you do to help us learn the fine art of travel hacking!

    Sending love and wishing you exciting travels,

  • Tara says:

    25,000 miles would be enough (added to my current AA miles) for a round-trip ticket to Australia this spring. 13-hour plane ride aside, I’m really looking forward to seeing this country in real life for the first time next year.

  • Emily M says:

    I came across your website last week after seeing your newest book in an airport bookstore. This is the website I’ve been searching for.

  • Kevin Senapatiratne says:

    I would use the prize to continue to teach our daughter about the joys of travel. The next destination we are working on is London.

  • Sean says:

    With the miles I would travel to North Carolina to knock off more courses in my own quest of becoming the youngest person to play the top 100 golf courses in the world. Getting closer!

  • says:

    awesome!!! With 2 young kids, my husband and I haven’t flown anywhere in a while – would love to take a vacay!

  • Nick D. says:

    We primarily fly with American because of their great mileage redemption options! An extra 25,000 would be really nice to pad out our account 🙂

  • Richard says:

    Would love to go to Southeast Asia!!

  • JG says:

    To visit family in L.A.!

  • Kevin says:

    I don’t where I would go with the extra 25K miles just yet, but I would definitely add an additional leg somewhere along the way of my upcoming RTW journey!

  • Sandi Malloy says:

    I promised myself a Tumi international carry on as a gift to me when an unwanted settlement became real. I now have the Tumi (found on sale at a very reasonable price at Travelsmith!). I want to go ANYWHERE a flight will take me to try out my Tumi. 25,000 points can make this a reality.

  • Bronwyn says:

    Neither I nor my fiance have ever been outside of North America, and we would love to go. Where? That would be such a difficult decision! We’ve barely ever left Ottawa. For years, every time I think, “maybe we can afford a vacation”, something happens and we have to use our savings to cover basic expenses. There’s been three different roommates from hell, two of whom didn’t pay their full shares, so we had cover thousands in extra expenses. This summer, our landlord evicted us so he could rent out the house on Airbnb for more money. In the process he ruined *both* the vacation periods I had booked this summer, with the harassment and house-hunting, and then we had to move house in the second one. Our case against him for harassment and moving costs is in hiatus, after a huge amount of effort: we have to start over on it. Now I’m being laid off in a month and I don’t know where our next income will be coming from, and I’m the breadwinner while my fiance finishes school. I am exhausted and terrified, and our new place looks like an exploded heap of boxes.

    I would really like something spectacularly wonderful to happen. I hope that we will win these miles and go somewhere beautiful and strange for our first ever adventure abroad.

  • Vincent says:

    I’m ready to take a trip!

  • Jeremie says:

    These miles would help tremendously to cobble my existing miles together to visit Gilda in Ecuador, a young girl I’ve sponsored for almost two years through Children International. I haven’t met her in person yet, but meeting her and her family is at the top of my list, as soon as work allows.

  • pat dowling says:

    I’m in

  • Justin Brunner says:

    Chris and gang,

    What a great giveaway! I’ve been banking miles on AA for a while, and using your hacking tips to book my first round-the-world ticket next year (hopefully)! It would be a dream to use these miles for a leg to London. I have two long-time friends who moved there about seven years ago and I haven’t been able to get there to see them. Although I’ve been invited several times, the timing (or cost) never really worked out. I’m sure they’d show me all the amazing historical sites, the old and new architecture and the great nightlife! It would be so great to have the chance to catch up with old friends in a culturally-rich city like London! We’d also trek out to the countryside, for sure. Thanks for the great opportunity! Fingers crossed!!

  • Cristine says:

    I would go to New York City and visit all the areas I was too much of a scaredy cat to visit when I lived there 30 years ago.

  • tiffany l says:

    i’d put them towards a first class ticket to the maldives on etihad!

  • Shauni says:

    You know what? I’ve been to a handful of countries, many of the islands in the Caribbean but can’t seem to make my way to Portland, Oregon. Why have I romanticized this place so?! Dunno… but I daydream about finding a cute miniature house off of biking, eating some good grub, and just exploring. So, that’s what I’ll do if I win 🙂 Won’t have any more excuses.

  • LISA LOCKLEY says:

    Would love to get to the furthest point those miles could take me… you inspire me and so many others. … to see the world and all its wonders!

  • Sabirah says:

    You’ve opened my eyes to see that miles are like a new currency to me. The travel currency, I call it.

  • Tianna says:

    Thank you for such a great giveaway! Hope I win so I can finally go to wizarding world or n’ahlins!

  • Kay Long says:

    All praise to the cat gods and may their favor continue to shine upon me.

  • Maria Valigurska says:

    Hi guys, i’m a normal girl with the wanderlust 🙂 winning these miles would mean for me an opportunity to realise my first trip outside the Europe, where I live. I’d love to meet an old friend of mine from Mexico, and discover all the beauty which Central America and The North America provides 🙂 some extra miles would help me to make my dream of Tour de Americas come true 🙂 Thanks

  • Alice says:

    As a college student in my third year, I am trying to gather as much information as possible about my options for my career when I graduate. I have wanted to work in health, and after traveling to Nicaragua, Panama, and Ghana in the past two years for global development and health volunteering and a global health internship, I want to make travel and health volunteering a bigger part of my life! The American Airlines miles would help me plan another more affordable trip to a country (I’m currently thinking about Thailand or Tanzania with an international health organization) to learn even more about global health systems, being a doctor, public health issues, and other topics that I want to work on in the future, a lot like how you started, Chris!


  • Troy C says:

    I would use the ticket and fly to Las Vegas. While in Vegas, I will win one or two poker tournaments for around $1,000,000. Then I will use that money to cross several things off of my bucket list. I will then continue to travel throughout the next year with my winnings. (Note: If I do not win the money, I will simply see my friends in Vegas whom I have not seen in quite some time)

  • Mantas Vidutis says:

    I need those miles, they are the only way I can get to Europe to save my kidnapped children.

  • Michele Pineda says:

    I would use the points to visit the Land of Eternal Spring… otherwise known as Guatemala. With family and friends there, it would be great to get away for a quick vacation and enjoy the food, the markets, the warmer weather, black sand beaches, volcanoes, and friendly locals. My job is pretty stressful but rewarding (LIHEAP program, helping those in need to heat their homes) and at the end of the season I am SO ready to get away and relax and this would definitely make me smile 🙂 Have a great weekend!

  • Ruth Amick says:

    Hi, Chris!

    I live in So CA.

    Congrats on your new book, and I hope you are enjoying the tour!

    I would use the miles to send my boyfriend to the Cheyenne, WY area. His parents live out on the plains not far from there, and he really needs to see his mom soon because she is not in good health.

    Good luck to everyone commenting. 🙂

  • Mia says:

    I’ve been reading your material and lurking online for years now. It’s so fantastic to be in a community of people who love travel and find a way to actually do it! I still get a lot of strange looks when I mention that I travel alone, but the fantastic experiences are certainly worth it all.

  • Bec Tilley says:

    I wanna travel from Tasmania to the USA next year to see my friends in Oakland who i met last year; do some circus, maybe go to Burning Man (though it scares me silly!!) and that’s all planned already, but I am also madly in love with NYC and the friends I met there so I would love to be able to go there as well, which is a bit out of my budget! If I had free miles I could do that as well, and more … maybe go somewhere new ^_^

  • Scott says:

    To paraphrase Dr. Seuss, oh the places I’d go!

  • Ben Paniagua says:

    Hi, Chris! It’s Ben from the Inkwood Books in Tampa. That night you invited me to WDS 2015 and ever since I’ve been beating myself up for giving into FEAR and making the excuse of vacation time a reason not to go.

    After seeing this post and seeing your “Be a Quester” video it really made me think about what you’ve been pounding into me all these years!

    I can’t think of a better deadline of July 2015 to have quit my job and focus on my travel startup. I’d use the miles to attend the WDS next year and tell you personally how my quest has fared. Help me make dramatic change!

    Ben Paniagua

  • Marama Carmichael says:

    OOOH I’d use it to either travel to the states with my family (which I’m planning for the end of October anyway) OR to see Japan (which my son would love to see next year) or …. anywhere really.

    This will me my 1st trip O/S. I’m in Australia which is a LOOOOONNNNGGG way from most places so airfares are obviously quite high.

    We’re going to Orlando so I’d extend the trip and see New York as well I think if we used it this time OR save it for the next one. I have the travel bug and want to go somewhere every year from now on – late bloomer 🙂

  • Sussi says:

    I there. I’m hoping to take a year off, to start :-), and travel the world with my son. But flying to the east coast next year to visit some dear friends would be a nice start.

  • Hannes says:

    I would love to win the miles because I’m saving up for a world travel. There are so much exciting destinations I could go with the miles 😉

  • Cimarron says:

    Ecuador has long been on the list…

  • Noamaan Nadeem says:

    I never win any of these, so why do I even bother. 72nd time is the charm?

  • Patrick says:

    Travel to new places is nice but I owe the family a visit. These miles could be my ticket! 🙂

  • Danielle Shubert says:

    It IS my goal to cover as much surface space as possible on planet Earth… but this year, I would be extremely grateful to have the opportunity to meet my husband’s elderly mom for the first time in Ontario, Canada and have a second marriage ceremony that she could be a part of.

  • John Fraboni says:

    I’d use it to take my wife back to her home town in Yucaipa, California. She’s always reminiscing about iur, and it kills me we haven’t been able to go since we wed.

  • Beidi says:

    This is going toward my trip to Thailand!

  • David Beach says:

    Not an exciting destination… and Im not just saying this.. I need to get to my parents place. Other side of the country. Im an LA actor… vacations arent easy at my level… and getting home is tough…
    And now.. I should be there for them. Just saying.. How cool for you to offer this though. Major kudos

  • Michael Young says:

    I promise to use them for good and not evil.

  • Steve Ramanauskas says:

    Wonderful contest, thanks– and would be very useful

  • Jenn Vargas says:

    I’ve always wanted a weekend in New Orleans for my birthday (which is coming up in a few weeks!). Sure it falls during hurricane season, but I’ve always wanted to try beignets 🙂

  • Adrien B says:

    Hi from Provence!
    I am a 20 years old faithful reader ! I am planning a trip across orth Amercia, these miles would be really useful !

  • David Orman says:

    Loving the book. Sharing it with others.

  • Mitsu Okubo says:

    I would love to go to Japan. I have never been and would love to reconnect with my family whom I havent seen in 20 years.

  • Marius says:

    I would like to surprise my wife with a magnificent trip!

  • Steven says:

    I’d love to take my cats to new paces in the PNW. Vote for your feline friends!!

  • Ada says:

    Dear cats and biased judges,

    I would love to use these AA miles towards a trip to Europe.

    Your fan,

  • Nicole says:

    I would use the miles to the banked ones I have for an around the world trip I’m planning on taking next year.

  • Morgan W. says:

    I am a videographer aiming to be a freelancer. I love the idea of working for a travel service. Whenever I travel I always bring along a camera, film and edit a piece for my reel. I currently have my eye on a trip to San Luis Potosi, Mexico to capture ‘Dia de los Muertos’ Pick me, please!

  • Edwin Zuniga says:

    Thank you for the opportunity, Chris! I’m currently saving up miles and cash for my first international trip to Iceland. This would help out a lot! Thanks again!

  • Linda S. says:

    My philosophy? Use miles to invite a friend with me on an adventure, then split the cost of my paid ticket to make it half-price (and still get the miles)! Or introduce one of my nieces to the thrill of travel. I might use these miles to take my youngest niece to Italy. And on the plane I will read “The Happiness of Pursuit”. Oh wait – I’m already reading it! (Is that enough blatant kissing up to get me the prize?!?). 🙂

  • aurea says:

    My way to express gratitude and give back is by doing poetic action, Mexico is having a hard time with violence so me and my friend want to get to Nepal to the novemeber silent retreat and from there start a project of peace and blessings towards my country. We will film every poetic action and interviews with peace makers from India to inspire our friends and community. We have being working really hard so it would be just a mayor sign and enormous gift to get this miles that will make possible this trip and hopefully create beauty for others .

  • Nichole says:

    I would get a ticket home for Xmas so i could give all my family and friends a copy of The Happiness of Pursuit as gifts – in person 🙂 . And also get in my (perhaps) last visit with my 90 year old grandmother before I set off on my RTW next Oct wherein i plan to share my fundraising and non-profit management skills with the developing world.

  • lauren says:

    This is a beautiful giveaway and thank you for always putting the giveaways on your website. I think I would give this away or use this as one step to new Zealand/figi which is a huge number one dream of mine. I also want to share this with my husband because he inspires me to dream and I want to learn all these travel tips to help him believe in the possibilities of a non conformist life. Thank you for all the posts you are an inspiration.

  • Jenni says:

    Great giveaway! I would use the miles to visit our family, or help us get to our honeymoon!

  • Eliza says:

    I’d use the miles for a one way ticket to Barcellona. I want to slowly walk the Camino de Santiago.

  • Mitchel says:

    My journey would take me to Costa Rica to visit the farmers and entrepreneurs I’ve lent to on Kiva. I’d love to see first hand their creative and hardworking spirit.

  • Rusty Handler says:

    I just recently got a job in Boston but my older sister is due to give birth to her first child around New Years in Los Angeles. I would use the miles to be able to jump on a flight the second I hear she is going into labor so that I could hold my beautiful niece.

  • s.w. says:

    I would love to visit Utah on of their national parks with my best friend (Zion National Park)

  • Shannon says:

    Exciting prospect. I haven’t been on a vacation for quite some time. This will help eliminate one excuse for not going. And, hmmm . . . . I think the most fun will be picking out the place to go. 🙂

  • Melissa says:

    Some where in South America! I’ve never been and want to go everywhere.

  • Samantha says:

    We’d love the miles! We’re on our second three month EU tour this year using AA miles I earned working my tail off – it would be a wild treat to win some and keep our adventures going!

  • David says:

    Currently my odds of winning are 1 in 222. Not bad.

  • Nick says:

    I’d love to fly to Asia (which I’ve never been to) on Cathay Pacific!

  • Keith says:

    There is a great workshop ai want to take early next year.
    Winning the miles would take care of the travel cost! Hooray!!!

  • Michelle Templeton says:

    Thanks for this! I would love to win as I’m collecting miles to get to Scotland to visit a beloved friend!

  • Susan says:

    Winning would help so much towards a dream vacation! Thanks for the chance!

  • Anna Lazowski says:

    I live in a city that, according to Time Magazine, was colder than Mars last winter. This would help me get the family to a sunny spot when the deep freeze hits again.

  • Casey Moynihan says:

    Hi Chris,

    This is pretty nice of you to be doing this!! Anyways I would use the miles to go visit my brother in LA. Go up to San Fran and see wine country. NY to do stand-up with my buddy. Sedona to relax. Nashville to see my buddies new baby!

    Thanks again,


  • Ed says:

    With winter closing in, any place warm and sunny would be a great treat.

  • James says:

    I would love to use the miles to further my nonprofit organization’s goals to help fight malaria in other countries!

  • Trevor says:

    Hey Chris — sounds like you’re on quite the trip for your book… Do you anticipate making it to DC or Baltimore?

  • MAX says:

    Hey Chris

    I just want to thank you because you’ve been a very influyent person to me. I’d love to win and if I don’t thank you anyway for doing cool stuff like this.

    I sincerely appreciate and greetings from Mexico.

  • Shelly E says:

    You are way too kind! A getaway would be Ah- mazing!!!!!!!!!!

  • Bobbi says:

    I would use the miles to visit New Orleans and continue to take photos of life in the moment. Love traveling and would enjoy seeing more of the world.

  • Nan says:

    My daughter just had a baby and lives in Phoenix!!

  • Wendy says:

    25,000 miles is very generous. I had to read the blog title twice to make sure I read that correctly. If the feline and human judges chose me out of all the deserving entries above, I would choose one of the following destinations – WDS 2015 (ticket still needs to be bought but there is no way I am missing next year), a trip back to SF to see all my friends and my cat Bella who was adopted by good friends when I left SF a year ago (Bella would not have survived a flight across country as 30 minutes wrangling in a bag is her limit), or tickets for my sister to take a trip anywhere in the U.S. she would like to go. It has been a challenging year for both of us and I wouldn’t have made it through this last year without all her help.

  • Nicole says:

    My friends & family are spread over a few continents, so it would be great to have miles towards a trip!

  • Neff Bonifacio says:

    Combined with the 8.000 miles in my account, I would fly to Lima just to have some authentic Ceviche with my aunt.

  • Deb says:

    My husband was diagnosed with cancer just 1 week after we got married. It forced us to reevaluate life together and put fun on hold. Now that he is cancer-free, it’s time to get back to life and living again. It’s time for fun!

    We are saving for a trip to Moab for an extreme adventure vacation because nothing makes you feel more alive than concurring things that scare you. 25,000 miles would help us kick butt!

    (Win or lose, thank you Chris for all that you do. Travel was something I used to only dream about, but your site has shown me dreams are only crazy if you don’t make them happen.)

  • Scott says:

    may the odds be ever in your favor

  • Grant Huhn says:

    Thank you for doing this, Chris… and for all the help, encouragement, and motivation you’ve given over the years. If I received the points, I would probably use them as a prize in a fundraiser for either my local high school (West Salem) or for a fantastic local non-profit (Salem Leadership Foundation). Here’s to living!

  • Michelle D. C. says:

    I would take my daughter to Cardiff for the Doctor Who Experience

  • colin says:

    I would use the miles to help get to spain for the camino de santiago. Ive been inspired by “life on foot” whose author/site I found through aonc –thanks

  • Steve Johnson says:

    great idea- thanks! 🙂

  • Julie says:

    This is truly an amazing giveaway! I would love to visit NYC again or maybe even use the miles toward my Europe dream trip!

  • stefanie says:

    I’d go to Australia next summer!

  • JustJohn says:

    Hi Chris!
    I just saw your interview on Nomadic Matt’s site and wandered over here to check things out.
    I saw this page and how could I resist giving it a try. 🙂
    I’m putting things in place to start my own pursuit and these points would be helpful.
    I’m enjoying your site and all the information.

  • Towaka Matsumoto says:

    I would love to win this giveaway! Not only would I use this for myself, but for my family and friends too! I’m still very young and it has always been my dream to travel the world and discover the beauty of the it and as difficult as it may seem, I am determined to pursue my goal. I still have a very long way to go and progress but winning this could be a wonderful first step as I have only traveled three countries, terrible for someone who wants to travel 🙁 !

  • Josiane says:

    I’d probably use those miles to go visit Portland again: I went once, briefly, and I want to experience more of it, with my love this time – I know he would really enjoy all the micro-breweries, among other things… Also, it’d be really cool to time that trip so that it coincides with either Pioneer Nation or WDS!

  • Mari Ohira says:

    Travelling is my religion!

  • Ramsey says:

    I’d use the miles towards my boyfriend and my annual international birthday trip.

  • Veronica says:

    I haven’t seen my brother and his family in almost 2 years – I’d fly to Florida for the Thanksgiving holidays. Good time to leave rainy Portland Oregon for that Florida sunshine!

  • Phil Burmeister says:

    Let the pursuit begin.

  • Matt says:

    I haven’t had much opportunity to travel, as of yet, and would love to see more places.

  • AJ Williams says:

    I love travel. Everthing about it! Even the waiting in airports, the delays, the lineups. I love it all. Especially the people watching and meeting new interesting travelers. Thanks American Airlines!!

  • Mal says:

    Trying to build up miles to go to Peru next year. Always wanted to hike the Inca Trail and eat lots of ceviche and play with llamas.

  • Monica Bourgeau says:

    Hi Chris – I would use the miles to take a second honeymoon with my husband in Hawaii 🙂

  • Gabriele says:

    Hi! I am Gabriele, an Italian medical student who wants to learn as much as possible of the best medicine around the world in order to provide the best care for the future people in need! 🙂 And like the majority of med students, 99% of the travel budget I have is for commuting… Help me discover new ways to improve our health system!!! ^^ G.

  • Peter Croce says:

    Hey, Chris! I would love to use these miles to continue my travels. After living in PDX for a year, I’ll be driving east to visit family in Florida then heading to France for a few months. From there, I’d like to visit SE Asia, and the miles would be a huge help. Thank you for curating an amazing experience at my first (but not last) WDS this year. I’ve already been evangelizing and created at least one more true fan. Keep it up, cousin!

  • Chris Sawyer says:

    I’ve done a good deal of traveling in my life. With these points I would send my wife, who has done very little traveling, on an adventure. That way she too can catch the travel bug and I can get a life-long travel and adventure partner. 🙂

  • Terry Wilson says:

    I’d fly to California to see my Aunt who I haven’t seen in a out 15 years. Thanks.

  • Helena says:

    This would certainly get me one step closer to being able to attend WDS next year! I’ll be coming from Slovenia!

  • john says:

    Thailand! Planning a year+ of traveling the world so these points would surely help! Thanks 🙂

  • ALBERT says:

    Hi, I’m traveling the world by bicycle for 3 years … Could be nice to fly home to visit family and friends whenever I wanted 😉

  • Michael Zagar says:

    I would love to send my overworked and underappreciated wife (a mother of 4 small kids) on a vacation spot of her choosing. And maybe she would bring me along too.

  • fadz says:

    I want to travel the I need those points! :’D

  • Marvin says:

    Hi Chris!

    “All that I am, or ever hope to be, I owe to my angel mother.” -Abraham Lincoln
    With your incredible tips, we’ve been able to make a dream come true and become full-time travelers. Thanks for being awesome. Right now, we’re ‘happily pursuing’ miles to fly my mother for her first time ever to Europe next year to meet us there and fulfill her dream of attending Easter Sunday mass with the Pope in Italy! These 25K will be tremendously helpful in making her quest to see the Pope a reality. Crossing our fingers that we can win the favor of your famous feline gatekeepers. 😉

  • Sese says:

    I’ve postponed it long enough….it’s Alaska time! Thanks for inspiring.

  • rob simpson says:

    These would go nicely with my plan to take wife to Hawaii! Thanks Chris!

  • Takki says:

    One day I might be the lucky winner. Maybe today???

  • Hunter McAlpine says:

    1) get north america map
    2) get dart
    3) procure a wall not too attached to
    4) Place map on wall with blue tack (already own)
    5) Step ten paces away from wall
    6) closing eyes turn an throw dart
    7) see if American Airlines even goes there.
    Sometimes the best things are not planned too much; besides South Dakota might be fun? Or wherever it lands.

  • Denise says:

    That would give me enough miles for Australia!

  • Jason says:

    Hi Chris! I’d love to win the miles so I could fly home to NYC and visit my niece and nephew!

  • Tom M says:

    I am new to the working world. I became aware of travel hacking during college, but never had the income or credit history to take advantage of the techniques. I did however make a point to get some low level credit cards upon turning 21 to get the ball rolling.

    Now, I am working as a first year music teacher. Despite my less than epic salary, I now have just enough buying power plus regular expenses to build a travel hacking portfolio.

    I want to cap off my first (hopefully successful) year of teaching with an epic adventure abroad, one I was not able to pursue over the past 5 years as a frantically busy, financially strapped college student.

    (Bonus: I could take the money I would have spent on a plane ticket and put it towards my student loans.)


  • Aaron H says:

    I enjoy reading your blog.

  • Alex says:

    Miles for free?
    Oh, how can this be?
    A contest so fine
    The reward quite divine
    An adventure awaits
    The cat seals our fates

  • Claire says:

    Hmm… I think I’d head back out to Utah to see more of its amazing national parks. 🙂

  • Nicole Bolek says:

    Carpe the (h-e- double hockey sticks) out of every diem! Thank you for paying it forward!

  • Sese says:

    No more postponing….Alaska time! Thanks for inspiring.

  • Andrés says:

    Hey, thanks for the giveaways they keep getting better!

  • Katie says:

    I haven’t been to the U.S four years. This is enough points to see every farflung place I desire.

  • Lavon says:

    A ticket for my niece to see and hopefully even volunteer at the Iditarod. She helped make blankets for the dropped dogs last year.

  • Nicole says:

    I’d use the ticket to book a first anniversary getaway with my husband…ideally to Peru & Machu Picchu. thanks for posting this giveaway!

  • Andrea says:

    I would go to Hawaii and photograph the rainbow eucalyptus trees so that I can paint them. It’s risen to the top of the dream/to do list!

  • Hannah says:

    Easy! The gulf coast of Florida for a wreck diving trip!

  • Jean-Philippe says:

    Hi, I’d really like to go rock climbing in Geyikbayiri (Turkey) and Kalymnos (Greece), so I guess I’d use the points for intra-europe travel after booking and award flight from Montreal with other miles 🙂

  • Jessica Ives says:

    My husband and I are planning to bike cross country in 2015 and we would put the points toward our one way ticket to the west coast!

  • Kathleen says:

    I have to make this quick to meet the deadline. This is an awesome giveaway and I love your books. The last few years have been very challenging for me and I would use the miles to see family and take a moment to re-center. Thank you for all you do.

  • Samantha says:

    To Istanbul I go!
    One more off the scratch map.

  • Jeff Moeller says:

    I’d go to San Francisco, the top city I want to visit in the US that I haven’t been to yet.

    Not sure if the deadline is extended, great giveaway Chris.

  • Linda says:

    I’d love to use these points to achieve my dream of going to New Orleans in February 2015. Mardi Gras falls on my birthday (Feb. 17th), and I’ve been dreaming for years to go there for my birthday. 🙂

  • Brent says:

    Chris, thank you for all that you do for this community and fellow nonconformists around the world.

    Reading through the comments it becomes clear that you have inspired so many.

    Thanks for all that you do.

  • malte says:

    wow 25000 miles that is awesome thanks

  • Rose says:

    Hi Chris ,like you said the possibilities are endless, so is my hope- hope of seeing the world, cherish my life journey and pursuit of inner happiness.

    By the way, thank you for all that you do and information you share with the world, I’m inspired. Best regards from Malaysia

  • Frances says:

    What fun! I’d go to Sweden.

  • Yayin says:

    Woww, 25000 miles is huge amount for me!! it’s so hard to earn big miles here in Asia countries.

    Thank you so much for the great giveaway Chris!!

  • Muuching says:

    One of my goal in life is to bring my parents travel abroad with me at least once in their lifetime (all the cost and expenses are all mine).
    This great miles would be a huge help for me to hit my goal faster. And I would be happiest if I’m able to let my parent really enjoy what the outside world could offer them.
    Awesome giveaway, thanks a lot !!

  • meichi says:

    Months ago, I’d told my family and friends I’ll start my solo travel (first time in life!!) to Japan in next year. I want to experience and see the world on my own. But above everything, I would like to search for ( or maybe build up) inner strength, courage and confidence, last but not least inner freedom.

  • Leong Choon C says:

    I really love this great giveaway- make everyone can fly, so do I, can fly with all the possibilities !!

    Thank you so much

  • Leonardo says:

    I would go to Maine to see the beatiful fall scenery and enjoy the tranquil pace of life.

  • Samuel Eatmon says:

    Thanks for this opportunity.

    I have always wanted to visit Japan but my wife doesn’t want to go, especially since the flights from here are so expensive. This would be a big help! If you pick me, I’d gladly give you an article about the trip… 😮

  • Cho Marzin says:

    I strongly believe travel is one of the greatest platforms for personal transformation. Travel broadens your comfort zone and pushes you to face fears and go beyond your limits. With the built up strenght and confidence over time, the development of internal power of exploring what’s possible seems endless.

  • Steve says:

    Chris, first of all, congrats on the new book and NYT charting!

    Winning these miles would definitely take me somewhere warm come January or February.

  • Chris Allen says:

    I would go to Hawaii. Thanks Chris!

  • Jeffrey Morgan says:

    I’d love to get a jump start on my travels. If I win I will vacation on the Big Island of Hawaii.

  • Stacy says:

    Thank you for offering up this contest. The past 18 months have been quite a long emotional journey for my family. It would mean a lot to me to be able to give this flight to my Mom to give her a chance at a holiday to get her mind off everything and enjoy herself for a few days. Thank you.

  • manda says:

    Love the giveaway! Trip with hubby.

  • Matt says:

    ooo, 25k would indeed enable me to have the babymoon with my wife that she wants. We’re that close to an upgrade.

  • Andrés Oliveros says:

    Hello Chris (from Monterrey, Mx). Reading The $100 Startup helped me leave my corporate lawyer job and start the first organizational storytelling consulting firm in México.

    I’m getting married next year and WOULD LOVE to win those miles :)))

    All the best, and looking forward to attend a WDS soon!

    -Andrés Oliveros

  • Viviana Martinez says:

    Hello Chris!
    If I win, I will use the miles for my honeymoon and fly to the french riviera! Drink wine and eat cheeese!

  • Barbara Martinez says:


    I would go to Hawaii <3

  • Madelynn Martiniere says:

    Thanks for this contest, Chris! Been a follower of your blog for quite some time now.

    Next two places on my list to travel are Nigeria and Thailand to write, hike, decompress, and research. Would love to use these miles to do so!

  • Adam Hansen says:

    This would be awesome! I could use a little getaway.

  • Betty Robinson says:

    Hi Chris,
    I am a amateur birder, would love to win the points to go to the Birding Rally Challenge in Peru.

  • dave romanyk says:

    love your new book!! Amazing!!

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