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How to Become a Travel Hacker and Never Pay for a Flight Again


I just booked a round of travel for next month, when I will be in India, Thailand, Vietnam, South Korea, America, Canada, China, and Japan. Despite the fact that these flights are in a few weeks, I paid next to nothing for them, as usual. Here are some examples from the end of my upcoming trip:

  • Seattle, WA to Springfield, MO – $20
  • Springfield, MO to Shanghai, China – $9.50
  • Shanghai, China to Tokyo, Japan – $14
  • Bangkok, Thailand – Free
  • Seoul, South Korea – Free

The first two flights involve a tiny airport that usually charges triple what a major airport does, and the cheapest airfare I could find for the third flight was about $800. The last two are considered “extended layovers” and are free on my way to another country. These fares are typical for what I pay when I fly. Nothing I did was complicated, but it did take time, flexibility, and an understanding of how the system works.

What I am presenting here is a very simplified version to get you on the right track. It will still take some time and effort, but this should lay out the first few steps to get you walking in the right direction. The process is just difficult enough to weed out the truly lazy, which obviously does not include you.

Let's giddyup!

Step 1: Frequent Flyer Programs

You can’t earn miles unless you are signed up for them. So sign up! It doesn’t matter if you are flying anywhere right now. I would say about 1% of the miles in my account were earned from flights, and the rest were taking advantage of the offers they constantly have.

Which Frequent Flyer programs should I sign up for?

I’m glad you asked. Ones that are based in the USA. America is renowned for having the worst airlines and the best Frequent Flyer programs, and you don’t have to be an American to take advantage of either. While you should definitely sign up for any and all reward programs (you can’t win if you don’t play, and there’s no downside), focus your attention into one or two programs based in the US.

You probably want me to get more specific.

There are three main alliances. Oneworld, Star Alliance, and SkyTeam. Whenever you fly on any airline around the world, you can earn miles on your choice of any airline in that alliance, and use those miles on any airline in that alliance. Pick one from each and direct all future miles into it, because you can’t merge miles located on different airlines. Personally, I recommend American Airlines for Oneworld, United for Star Alliance, and avoiding SkyTeam altogether, because your life will be a lot better if you avoid Delta and its friends. Mine certainly has been.

Step 2: Fill them up!

There is an ever-rotating way of getting miles into your account, and this is the part where you start to choose how obsessive you want to get. When I first started I just focused on huge chunks of miles every now and then. Now I have a routine going that keeps a constant small flow of miles into my accounts even when there are no huge chunks, and it doesn’t take much time. There are people far more obsessive than me, but I travel to live, not vice versa.

If you are an American citizen, it’s exceptionally easy to get hundreds of thousands of miles quickly through signing up for new credit cards. Even if you aren’t, it’s still easy to get at least 25,000 miles every 3 months, which is enough for a round-trip ticket. That’s at least 4 trips per year just waiting for you to take them, and providing you aren’t the kind of person that fills up every credit card you touch, it’s basically risk-free.

I will give you the keys to these a little later on; first we need to finish the overall understanding of how the system works. Once you get the miles flowing into your account, you can find more and more ways of doing it, like making your everyday purchases through airline malls and credit cards to get paid for doing things you are already doing.

Now you're flying with power!

Step 3: Cash in those miles for flights!

While it seems like this should be the easiest step, it is usually the most complicated. While the first two steps require tenacity, this one requires flexibility and investigative skills. To be crass: never pay retail.

Now that you have multiple accounts with miles sitting in them, you have options. Use this fact to your advantage. Different airlines charge different amounts for different flights, and it’s rarely consistent. Do some research and find the cheapest option. Here are some general rules:

  • Always get the saver rate, which is usually half or less of the standard. Even if the website doesn’t say it’s available, call and ask. Sometimes it’s just not listed yet.
  • Be flexible with your times and days. I was able to get an $800 flight for $14 because I could move it a day earlier. If I insisted on going the initial day, I would have had to pay the full cost.
  • If you have the miles, don’t be shy about going business class. Typically it’s only a 30-50% increase in miles to get a business class ticket, while paying cash would be a 500-800% increase in the amount you pay. It’s a much better value when you use miles, and can open up much better flights and times. My last flight to India was business class, and getting to lie flat in a private bed with a massive TV screen and great food was completely worth it.
  • Don’t use miles if it’s a cheap flight. Miles are typically valued around 1¢ each. You should always try to pay less than this and get more value than this when you spend them. If a ticket costs either $200 or 25,000 miles, just pay cash and save your miles. What would have been an $800 ticket to Japan cost me 10,000 miles (plus $14 service charge), which is 8x the face value. That’s a good deal.

Finally, don’t be hard on yourself in the beginning. It’s like learning a new language or exploring a new city. You will make mistakes and not know where to find the best deals and flights at first. Don’t let it stop you. You will still be getting a far better deal than if you hadn’t done it, and you will learn more for the next time.

You'll be here in no time.

Now, here are the valuable resources you need to get started.

Frequent Flyer Redemption Options – Just plug in the cities you want to visit, and it gives you a complete list of which programs fly there and how much they cost in miles. Invaluable for comparing options in Step 3.

The Matrix – This is where I always start looking for what flights are available. You can’t buy flights here, so no airlines are blocked, which is a big advantage on every other search engine. In addition, they have a timebar view that is priceless for understanding and comparing flights. Check it out and you will understand why I always come here first.

Become a Frequent Flyer Master – If you are ready to take the next step and devote a little time to getting good at this, here is your easy-to-read manual. It guarantees at least 25,000 miles just from reading it, which is a free ticket, and will likely give you that many times over. It’s honestly a great book, and taught me a lot about being a travel hacker, along with its companion, Become a Travel Ninja, which you can add during checkout.

Become a Travel Hacker – If you want the benefits of travel hacking without the work, this service scours all of the new deals as they happen and emails you the best ones. The first 14 days are just $1. This is the easiest method, and while you will miss out on the smaller and more complex deals, it’s a great time saver if you don’t want to dedicate the time to being obsessive about this.

FlyerTalk – This is the ultimate forum about travel hacking, and it’s completely free. I’m telling you about this here, but it shouldn’t be the first place you go. They speak in heavy slang there, and it will take about a month of reading and researching before you finally understand what’s going on, providing you have that kind of patience. If you want to become a master, young grasshopper, this is the place to learn.

List of Credit Card Offers – This is a simple, direct thread on FlyerTalk that keeps an up-to-date list of the current offers, so you can decide which ones are appropriate for your Step 2. There are always differing theories about which are the best ones, so pick some of the ones that seem the most valuable to you, and just go for it.

The Points Guy – This blog is obsessive about finding all of the deals out there and giving you tips about how to use them. It’s a little more accessible than FlyerTalk, but is still a firehose of information if you don’t yet know what you are looking for. He leans toward the high-end hacking, usually flying first class, but doesn’t let the little deals pass by.

Take your first baby steps

This should get you started on your way to becoming a prolific Travel Hacker who never has to pay for a flight again. I recommend opening some Frequent Flyer accounts, signing up for a few credit cards with no fees, and seeing how easy it is to get a bunch of miles. Use the Frequent Flyer Redemption Options to find out the best use of your miles on a trip you’ve always wanted to take, call them up, and book it for a small service charge.

Boom, you are on your way.

If you want to go deeper and find out all the other ways to get free flights, get the Become a Frequent Flyer Master book. Not all of my free flights are from miles. If you like the free flights but don’t want to devote the time, sign up for Become a Travel Hacker. Either of those will give you what you need to keep a steady supply of miles ready to use for dream vacations in the future.

I’ve been to 17 countries across 4 continents in the last 7 months, and paid for very few of those flights. It takes a little time and effort up front, but once you get rolling and see how easy it really is to get free flights, you wonder why everyone doesn’t. Should you decide to go on a big trip, check out my article on How To Pack To Travel The World Indefinitely. Now get started and let me know about your successes!

7 Lessons I’ve Learned From 7 Years On The Road

Hang on tight!

I’ve traveled my entire life. My first memory is, no joke, of a hotel room. My childhood had a lot of waking up in random hotels and coming up with a plan to explore and entertain myself for the day, as my parents regularly traveled for work. The love of adventure stayed with me, and I’ve always found ways to keep it a significant part of my life. Over the last 4 years, I’ve spent more time traveling than home, and a year ago I got rid of “home” entirely, just traveling place to place.

When nowhere is home, you begin to see the world in a different way. There is no vacation to escape to, and no place to hide and stagnate. Every day is a new adventure as you figure out how to survive in a different culture. There are some undeniable truths that I’ve slowly figured out along the way, and they are useful whether or not you are traveling. I’m going to share these secrets with you in the hope that you can use them as well. Some may seem like common sense at first, but pay attention for the new twist.

So much cookie!

Smile at children

It doesn’t matter the culture or language, I have never encountered a child that doesn’t light up when you smile at them. Even parents light up when they see their children happy. Nothing is a better icebreaker or friend maker, and it will brighten the rest of your day.

Introduce yourself

It’s easy to hunker down into your cocoon during travel and interact as little as possible. Introducing yourself makes the person crammed against you human, and makes you human to them. You want a human next to you when you need their help to awkwardly slide past to get to the restroom. And who knows, maybe you will have something in common.


Every chance you get. Take the stairs. Walk to the restaurant. You can’t interact with the world from behind the shatter-proof glass of a car, you need to get out there and experience it.

Hold 'em, Fold 'em, Run? Give me some answers, Kenny!

Play games

Card games, board games, limbo, dodgeball, it doesn’t matter. When people are focused on playing a game, everyone forgets about the awkwardness of making new friends. I once used Monopoly Deal (one of my favorites) to break the ice with some bunkmates on a train, and we ended up spending the next two weeks together, traveling through different countries every few days. Each night we would play a few more rounds as we learned each other’s strategies and shared stories, our friendship growing tighter as we subliminally picked up each other’s worldview.

Accept that you can’t do everything

Don’t try to squeeze something into every second of your trip or you will just end up burned out and exhausted. Fit sleep into your schedule, a full night’s worth without setting your alarm. You will be amazed at how you make better, faster decisions and have more energy to take advantage of your good fortune. It’s far better than missing everything because your brain is churning away on low fuel and too much stimulus.

Take every opportunity

“When are you going to be back?” became a mantra between a friend and myself whenever we debated whether to do something. Even the little things become much more significant when you put them in the perspective that you may never be able to do them again.

Make every opportunity

Don’t wait for the $10 pubcrawl to start. Go to a hostel lounge and start one yourself. Walk down unfamiliar streets and loudly proclaim the historical things that happened there with far more assurance than you should have when you are making something up. When you make your own fun, you start the momentum that causes everyone else to follow instead of mindlessly flipping through guidebooks looking for something that doesn’t seem boring.

Dancing in the snow, just daaaancing in the snooooow!

Don’t wait to travel to view every day as a new opportunity. The city you are bored by is someone else’s dream vacation. Make it yours, too.

Gurgaon, India: Minimalism

I moved apartments and had to spent a few days in a little hotel. I also explain baths as a kid and minimalism for me.