How Do You Pay for Your Travel? Part II

Monday’s post was about how I paid for much of my travel to 193 countries by being intentional about priorities and practicing selective frugality. Today’s post continues the story…


I didn’t begin travel hacking until long after I began traveling. At first, I did what everyone else did—I had a couple of Frequent Flyer accounts, I looked online when buying tickets, I tried to comparison shop and get the best deal I could, but I didn’t know much about the tricks of the trade.

One time, early in our years of living in West Africa, Jolie and I were coming back on a trip from Amsterdam. A Delta agent at the gate took our boarding passes and exchanged them for new ones. “You have been upgraded,” the agent said.

“Wow,” we said when we boarded the flight and went to row 4 instead of row 40. “This is nice.”

After that experience, I began to wonder if there was anything I could do to gain an advantage over the average traveler. The next year we wanted to go home for Christmas, and I discovered if I bought SkyMiles from someone on eBay (technically against the rules, but Delta didn’t care at the time), I could arrange to fly in Business Class all the way from Cotonou, Benin to Atlanta.

When we transited through Paris, I felt like a luxury traveler. Everyone always talked about how terrible Charles de Gaulle airport was, but we went straight to the Air France Business Class lounge and found it highly relaxing.

I walked around the lounge in awe, picking up all kinds of free stuff.

Can you believe these croissants are free? (I’ll have six, please.)

The cappuccino machine is unlimited? (I’LL TAKE ONE MORE!)

Funny how these things work: two years ago I went back to the same lounge while transiting to Central Africa and was amazed at how small it was. The croissants were stale and the cappuccino machine was unexciting. Lesson: Appreciate what you have, while you have it.

After we moved back to the U.S. and I started traveling on my own, the search for cheap travel took on a quest of its own. I went on a “Circle Pacific” trip to Asia, making five stops, experiencing new countries along with new airlines. I began collecting spoons from each airline.

These days, the Starwood Preferred Guest card offers a bonus of 25,000 points just for getting it—and you can also get the Business version to earn an additional 25,000 points. Bam! Back then, though, I was happy just to have the card and earn one point for every dollar of spending.

I was also a big fan of Priceline, a service I don’t use much anymore. In those early days I spent most of my trips staying at hostels and budget hotels, but at least once a week I’d use the “Name Your Own Price” option to book a room in a nice place. I didn’t have elite status and wasn’t collecting hotel points (aside from the Starwood card) but I was still enjoying the benefits of low-cost travel.

From those experiences I started branching out and learning more. No going back!

Round-the-World Tickets

After the Circle Pacific trip through Asia, I learned more about Round-the-World tickets. At the time you could purchase RTW tickets that were valid up to 20 segments, and I regularly used all 20… over and over.

I learned that it would be much cheaper to begin the trip from another country, so I began RTWs from Japan, Korea, and Sri Lanka.

I don’t buy as many RTW tickets now, but I still purchase at least one a year. In January I’ll be doing a two-week trip from South Africa to Qatar to Malaysia, eventually returning to the U.S. before continuing on later. In some cases, the tickets are still a great value.

Frequent Flyer Challenge

After getting the Starwood card and using it for years, I began to have more business spending—so I picked up the AmEx Business Gold card as well.

Then, I started getting Citi cards—several of them. I learned that Citi offered a plethora of different card products, all tied to American Airlines. You could get a Visa, Mastercard, or American Express branded Citi card—and you could also get a business version of each one!

Each card offered a signup bonus after completing a low minimum spend (usually $750 in 90 days). Furthermore, many of these cards could be acquired repeatedly. After having one of the cards for a few months, you could simply cancel it (or just stop using it) and successfully apply for a new card with a new bonus.

This was fun. I was shocked when I continued to be accepted for the cards, and continued to receive the bonus, as much as 75,000 miles each time.

These days, you can still earn bonuses on the Citi American Airlines cards, but not as many as before and for not as many miles. Still, the whole experience got me thinking. Were there other cards? How could I replicate this experience on a grander scale?

This led to the original Frequent Flyer Challenge where I applied for a dozen credit cards on the same day and was accepted for each of them. This practice is fairly common now (a number of bloggers write about it a few times a year), but at the time it was fairly new.

I received a lot of criticism for opening all the cards, and then I received a lot of miles and points. 🙂

If you’re curious you can read the most recent Frequent Flyer Challenge results, along with several other posts, in the archives.


AONC Travel Archives
American Express Enhanced Business Card
Citi American Airlines Cards

Why Write About Travel Hacking? Because Traveling = Freedom

Sometimes when I write about travel hacking, I hear from readers who don’t get it or don’t think it fits well with the rest of what I write. I understand the complaint, but I also think that a blogger should write about whatever he or she wants.

If I start thinking about how people will respond to any particular post, I won’t be very motivated to keep writing. Better to focus on the people who do get it, and keep moving forward.

As I see it, the connection between travel hacking and everything else I do is freedom. For the past decade I’ve been able to go anywhere, anytime. The opportunities are endless and the possibilities wide open.

Next week I’m heading to Australia, one of my favorite places in the world. My trip there is an award ticket on Virgin Australia, and I’ll be staying in hotels on points for my first three nights.

I don’t have a ticket back, and I’m really not worried. Because I have enough miles (in several different accounts), I know I can figure something out.

Miles are for spending, and travel hacking provides freedom.


That’s all from me. How about you?

We heard from a number of readers in the first post earlier this week. Has travel hacking helped you?

Feel free to share in the comments.


Image: Lena

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    • Paul says:

      Just wanted to say that the reason I started following your blog (in the early days) was about the travel + freedom concept. I have a good, location independent job, and never really needed the entrepreneurial/inspirational aspects. I really appreciate the solid, concrete tips about better travel or time management while on the road. More, please!

    • Kimmy | AfterGlobe says:

      I’ve used travel hacking to get many free flights for myself and others. It really helps to get you places you may have thought you couldn’t go to before. I’d love to get in on the Vanilla reload card travel hack, but unfortunately they don’t sell them in the Pacific NW. Thankfully, they are plenty of other things I can do until I’m in an area that has them.

    • Christopher says:

      Hi Chris, I’m a fan of your site, and travel-hacking. I applied for the British Chase card back when it came with 100,000 miles, and put a ton of purchases on it over a project, have over 300k miles sitting there, now. Still have to figure out using them on partner airlines, as the BA fees are ridiculous, and they have zero award availability out of SF.
      But last summer I flew SF-Lusaka-Togo-Paris-SF using 105k United Miles (a GREAT program compared to BA) and fees under $200. And now I’m flying to Khartoum, Sudan to start a 4 month bicycle expedition ending in Capetown. And I’m flying First/Business all the way for 65k United miles. Just the 2 free checked bags/ 140 lb. allowance that comes with that ticket saves me tons as I have to bring gear for 4 months of cycling. Fees= $80
      Long and short is I’m looking at all angles of earning miles; it’s not that hard. Helps if you have a business with purchases, but other things work, too. Just missed out on Sears 16 miles/dollar offer: I had a new fridge, a boiler heater, computer, etc. lined up that would have earned 128,000 miles had I pulled the trigger in time.
      Thanks for your ideas and enthusiasm for living and travel.

    • Mike Rudd says:

      Always great to see the travel hacking posts! You and Daraius from Million Mile Secrets really opened my eyes over the past few years to more than just frequent flyer miles.
      This year we got the SW companion pass and using Chase points were able to get about 16 RT domestic flights (busy year for weddings for us!)
      We also got about 10-12 free nights at Marriott’s. Just restocked w the Starwood AMEX business, Chase Ink Bold, and Citi Hilton (which we plan to stay at the Waldorf in Rome w our two free nights at the end of a tour in Italy…would never pay for it but free…okay!)

      My point…
      THANK YOU first off…and to everyone else…it can be done and you will see benefits! Plus it’s fun…just pay those cards off each month everybody!

      Happy Traveling to all!

    • Karen @ says:

      Travel hacking articles are the best part about reading your blog! Maybe if it wasn’t called hacking, people might feel better about it. It kind of makes a person think of a computer hacker – like you’re breaking into something. I definitely hope to apply to several credit cards with bonuses in the very near future when my income meets the criteria! I haven’t seen enough of the world but with a spouse and three kids you need a lot of points!!

    • John Spinhirne says:

      Ever since attending WDS 2013 a lot of what I thought I knew went out the window which led me to here, travel hacking. It led to other things but that is a different story. I joined the Travel Hacking Cartel and set a goal of going to India in March of 2015 for the Festival of Color. This will be my first trip out of country and I plan on making the most of it, mostly by getting my plane tickets for free and hopefully most of my hotel stays. I am also going to try a lay over for a few days in Germany, something I would never thought of if you hadn’t written about it. So here is to travel hacking and to Chris and his team for helping me and others live our lives.

    • Sue MK says:

      I enjoyed your article – made me think about a couple of options i have passed up recently. Have a great time in Australia Chris.

      from Sue in Queensland, Australia

    • Yvette says:

      Chris – I love the diversity of your writing. It often hits on things that are on my mind. I’m really enjoying the Adventure Capital course as well. Have fun here in Australia. The weather is fabulous and there is so much natural beauty to enjoy. Thank you for sharing so generously.

    • Larry Hochman says:

      “If I start thinking about how people will respond to any particular post, I won’t be very motivated to keep writing. Better to focus on the people who do get it, and keep moving forward.”

      Love the imagery of traveling on the wings of frequent flyer miles and accounts. But that quote of yours is the one that did it for me. A saying my wife and I have about our business…

      “I’m looking for people who are looking for me.”

      Very cool. 🙂

    • Tony Peters says:

      In no way should you disregard “travel hacking” articles/essays. I agree, the people who don’t get it, oh well! and keep it moving.

      Geez, I wonder do ‘they’ watch one specific television program also?


    • Marti says:

      Hey Chris, I like your approach to your blog. And I learned something from this post… about starting RTW from another country. Since I’ve purchased some of your travel materials, the information is probably in there… but today, I comprehended that little nugget.

      I have miles sitting in numerous accounts and lots of Starwoods and Hilton Honors points waiting for me, as soon as I figure out how/where to use them, which should be soon.

      And as soon as I can establish an income again, I may try your challenge. I am a believer in using the system as you can.

    • Gene Davis says:

      I love the idea of travel hacking. It will surely get me out of my local city for much wanted trips. But from everything I have read so far, you need credit. Which I have, but none of it good. While I am in the midst of rebuilding, what are the options for people like me who aren’t able to get a credit card to earn miles? Any suggestions.

      Thanks for the posts. I enjoy reading them.

    • Brent says:

      I recently saved over $2,200 on a pair of plane tickets to do a 4-city tour because I used points that I earned through my American Airlines credit card where I got a big bonus for signing up. This re-energized me to get back into big time travel hacking to save money on traveling!

    • J.R. says:

      I don’t think travel = freedom. Plenty of people travel no where at all and like you, believe they are “free”. Traveling then, it something else.

      Perhaps “opportunity taken”. Specifically, “travel opportunity taken”. The inverse is also true, “travel opportunity not taken”.

      Traveling is also “experience”. But experience doesn’t mean freedom either.

      Look back over history, before traveling became vogue. People thought that they were “free” then and enjoyed many freedoms. Many never left the homestead for example…

      Freedom must mean something else other then traveling. It’s a important distinction (critically important imo). Your software does not allow enough room for a full response – but freedom is all of the following: choice, responsibility, autonomy, opportunity, acceptance, respect, tolerance. All of these attributes and more describe freedom. You really can’t have freedom without all of them.

      However, “traveling” isn’t in the list anywhere. The choice to travel is – whether you go or not. The distinction matters quite a lot. Choice conveys opportunity, responsibility and so much more. Freedom is doing the things you want – and accepting ALL the consequences.

    • Chris Crompton says:

      Just wanted to say that not only have your books and blog posts inspired me, but they’ve helped motivate me to live a fuller life. I’ve got my own blog finally, and although it’s a similar focus, it’s my own take on life. I’m also beginning to travel more, which is something I’ve always wanted to do. So thanks for the inspiration!

    • Fazal Ilahi says:

      Wao amazing story of yours travel Journey.
      And I am going to look previous 1 Part of your travel story.
      I always Wanna Be Like You are doing travelling so One day I will do same.
      btw Thanks For telling us your story and You gave me courage for my travel journey.
      Always Be happy.

    • Eric Johnson says:

      Hey Chris,

      Great post. What is different now from when this post was written 2+ years ago? Do you use different credit cards? Any new strategies ?

      Thanks! See you at WDS.

    • wordcounttool says:

      Thank you for sharing your article. It was really great to read it. The pictures are really nice.

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