Last week I was asked twice about travel hacking, an occurrence that isn’t necessarily few and far between. Each time I think to myself, why not do a quick writeup on the subject so I can pass along the basics to others? At the end of the day, there is nothing I’m unwilling to share on the topic. Everything I’ve learned has come from others.

So here we are. Travel hacking 101.

I never knew about travel hacking until the first World Domination Summit back in 2011. It was there I was made aware of the impacts and inroads Chris Guillebeau had been making in a new breed of entrepreneurial spirit. Full-time travelers, life hackers, professional bloggers and life coaches, spiritual leaders, creatives. It was eye opening to learn about this trend; the tricks and tips to make hacking your travel worthy of something special.

Before I continue, let’s be clear that what is described below has worked very well for my understanding and execution on the topic, but doesn’t necessarily mean that you’ll find the same success (or even decide it makes sense for you). And that’s ok. Adopt a few approaches. Share with friends. Adapt a strategy that works for you.

The Premise

In general, travel hacking is a way to make your typical expenditures work for you in more than one way, and in this case, through some sort of travel-inspired component. It is both an art and a science. Rewards may materialize through credit card bonuses, hotel incentives, vouchers, targeted spending, or other various offers.

Travel hacking comes with a very real component of both personal responsibility and an ongoing attention to detail. Meaning, if you’ve struggled with over-spending and debt, you likely want to steer clear of these techniques.

With regards to a detail oriented mindset, you’ll need to stay on top of offers you’ve signed up for, fulfillment periods, airline accounts, and more. Speaking from experience, you can and will be burned by being too lax on the fine print!

Establish Goals

Before opening a couple credit cards or various airline mileage accounts (free), think about your primary goals. Do you and your partner want to travel abroad? Maybe you travel domestically frequently for work or personal interests and you’d like that to open up a few opportunities? Perhaps you want the freedom to take a trip across the country but also hit that spot in Europe you’ve been eyeing?

Establish for yourself a current hack that you’ll then decide how to execute using this information as a starting place. Don’t overdo it, either. There’s no need to open a handful of credit cards, aiming to do everything at once. Focus on executing one goal at a time, especially at first.

Rewards Sources

Credit Cards

Hands down, credit card rewards have been the primary way I’ve hacked travel over the last few years and thus will be my focus. This generally involves browsing current credit card offers, understanding signup bonus structures (10,000–50,000+ miles/points), comparing supported airlines, and making notes on those specifics based on where you want your travel goals to take you.

Since 2011, I’ve executed various goals with Southwest, American, and United. Each serving their own purposes, I researched the incentives of the time by comparing offers, understanding their rewards charts (here are charts for AmericanUnited, and Delta to get you familiar), and deciding the best move.

Of note, a helpful lesson is understanding which airlines belong to specific alliances. Here’s an incomplete but basic list that serves as an example:

Star Alliance Member Airlines:

  • Air Canada
  • Lufthansa
  • United

One World Member Airlines:

  • American
  • British
  • Malaysia
  • Qatar

SkyTeam Member Airlines:

  • Air France
  • Delta
  • KLM
  • Korean Air

A lot of bloggers and various travel hacking introductions will suggest that you open up a credit card and airline mileage account under each of the major member alliances, but I don’t necessarily think you need to do that if you have very specific goals or are just getting started.

If you see this as something that becomes more of a lifestyle, well, you might just want to do that. For everyone else, I believe the awareness is enough.

Beyond credit card bonuses there are a few additional advanced—and admittedly a bit mundane (however successful)—paths to racking up points for travel. One such example lies in really understanding your credit cards’ rewards programs. I mean really understanding them.

Points Grabs

Let’s say you have a credit card that provides 5x points when the card is used at office supply stores. Armed with that knowledge, you go to town and buy $1000 worth of gift cards for various venues you use regularly. That’s effectively 5,000 points that you’ve just earned. Interesting, right?

Believe it or not, there are rather consistent blog posts explaining the latest trends in points grabs similar to this. Whether that’s racking up extra points at a local retailer, writing yourself cashier’s checks, or even ordering money from the US Mint only to deposit it right back into your bank account*, there’s always something new to try out.


Some daily use credit cards provide excellent return on dining. If you have an active eating out mentality, double check which cards (that you may in fact use casually, not aiming for big bonuses) provide the opportunity to gain points on places you potentially already dine. You’d be surprised how methodically selecting the way you use your card(s) slowly racks up a significant amount of airline miles over months of use.

For more ideas and an updated strategy on points usage well beyond signup bonuses, check out The Points Guy. A longtime favorite by even the most serious hackers, the site features everything from new credit card offers, to valuations of airlines’ mileage programs, to dining out strategies.

Using Rewards

Once you have a plan in mind it’s time to get to work. Here’s an example.

At its apex, the Southwest Airlines hack could potentially provide free** travel for you and one companion on any flight during the duration you hold the Companion Pass—which ultimately boils down the the remainder of the year with which you attain it plus the entire following calendar year.

In other words, if planned extremely well, one could potentially have their partner travel with them, fare-free, for almost 2 years. And at last check, that companion can be changed a couple times during the time you hold the pass.

At its height, both the personal and business cards have offered 50,000 points per signup (after meeting a minimum spend). At the time of this article, they’d trickled back down to only offering 25,000 bonuses on signup, but keep your eye out for this fluctuation throughout the year and pounce when the time is right.

Assuming you have the ability to signup for both cards—personal and business—you would theoretically gain a quick 100,000 points after meeting the spend requirements, which are typically about $2,000 per card in 2 months. Additionally, the Companion Pass status is reached when your account reaches 110,000 points, a goal very doable if you plan purchases accordingly.

Maximize the two month window to cash in on not only the points for your own use on Southwest, but remember, your chosen companion can grab a seat anywhere you go, too.

Even if you don’t have a small business you can open the second card under, we’re still talking about up to 50,000 points for travel on Southwest with a very minimum spend.

Southwest’s domestic routes are not only very frequent but they’re also very affordable. At a quick glance, I could fly roundtrip to Portland from Denver for under 15,000 points in early October, for example. It’s hard to ignore Southwest’s domestic offerings.

If you want to geek out even more on the specifics of this offer, I stumbled across this post that’s already taken care of the math from just a few months ago.

Spending Strategies

One of the biggest stink eyes I get when talking about this topic is the defense that the travel is not really free. And in their defense of being defensive, they’re right. You have to meet minimum spends to attain these rewards. You are paying for something that is giving you the things you need plus a big bonus.

The last thing I ever suggest is getting a couple cards and raking up spending on things that you don’t need. If you think you’ll only really need to put $1000 on a credit card over 3 months, but the offer you’re working with is $3000 over 3 months, there’s no reason to put yourself $2000 in debt just to grab airline miles. Buy the ticket instead.

That being noted, really terrific spending strategies come back to the goal in mind and the offer you’re going after. Once you have those lined up, consider the minimum spend and decide how to execute that over the ~1-3 month spending period.

Think about groceries, cell phone bills, gas, upcoming purchases (a new computer, appliances), and other things that will be an expense whether or not you have a credit card to give you something back. Line those up with the card that rewards you the greatest for those things you’ll be purchasing regardless.

Pro tip: if making big purchases, try going through your credit card’s online portal that rewards you even more with 1x, 2x, 3x+ points on each dollar. Sometimes this can pay off handsomely.

Everyday Spending

You may read about credit cards that offer you this or that, but very rarely do you read about cards that could be used as an “every day spender” in the same articles. Being that the general strategy in all of this is being smart with your spending decisions and giving yourself the greatest opportunity to rack up travel rewards, consider a card that fulfills a large majority of your goals on a daily and weekly level.

Meaning, what card—beyond an initial bonus—could potentially set you up for the greatest rewards and overall flexibility for said awards based on your current and future spending habits? This may come down to how much you spend on groceries and gas, or on office supplies and nice meals with clients.

Spending the majority of your monthly expenditures on that card, and paying it off every month, can be a great strength in your travel hacking arsenal.

Travel Hacking Failures

When I initially dug into the world of travel hacking, I was not only enthralled at the opportunities but also admittedly uneducated on utilizing my rewards efficiently. Here’s an example of what not to do.

When I first began I went after an American Airlines incentive for both my personal and business cards. I gained a lot of points quickly and suddenly found myself staring at a big number in my AA account. I was giddy.

But what I wasn’t was educated on how to best use those miles. If we take a step back and think about it, American is a part of a large worldwide alliance. They fly to all corners of the globe and send their fleet to places I’d love to explore.

But what did I do?

I upgraded myself to business class (often draining 2x+ points) instead of sticking to the cheapest economy ticket to Hawaii, spending a week with my friend to celebrate his birthday. And in an instant, all of my work grabbing miles and following through on spending strategies was gone. I’d just about dropped my account to an unusable amount of miles. It would be a while before any additional travel could be had.

Truth be told, I ultimately closed those accounts after minimal use beyond that trip. I’d realized what I’d done. I didn’t have a travel goal and therefore I was floundering when the points were available. It was a token rookie and directionless mistake in the world of travel hacking.

Don’t let this be you, too! Business class is lovely, but not at the expense of (in my case) another free trip.

Credit Scores

Before I wrap up, let’s chat briefly about credit scores. First things first, if you had terrible credit, you may not receive the top credit card offers. You likely won’t be targeted and upon applying, you may not be approved.

But as far as the average score, or someone with a slightly higher credit score, there is often a fear that opening multiple credit cards will drop that number. Preventing—these voices have mulled—the ability to buy a car, a house, etc.

But in reality, as Chris Guillebeau proudly notes:

Managed well, there’s no easier way to quickly rack up the miles than with credit card signups. Your credit score will actually improve over time with more applications—I’ve seen it over and over.

The strategies behind travel hacking do not encourage opening and closing multiple credit cards in rapid succession, either. On the contrary, it’s built upon selectively opening and using various cards to maximize their potential over a long period of time. Once more, when paid off on time you’re actually doing a service to your credit.

Further Resources

So much of what I know has come from a handful of sources, and I continue to learn from these and other sources every year. Here are a few of my tip of the iceberg suggestions to help you get started with your next adventure:

No matter your goals and ultimate involvement with travel hacking, I’ve always felt it opens doors for many people that would have otherwise not traveled to places they’ve only dreamed of. And why not fulfill your dreams?

So what’s my next big hack, you ask?

Japan 日本, during cherry blossom season, in early 2015. I have my flight paid for with points. And if I play my cards right—which I now know I will—I’ll be left with more than enough for another international freebie, too.

Happy hacking.

* This is an outdated points grab strategy, but one that was actually live for a limited time years ago when ordering coin money via credit card was possible.

** “Free” typically means airfare free, sans required security fees or taxes. For example, it’s typically $5 one-way to travel on Southwest even when paying with rewards points.

Enjoying Spirit by Design?

Receive the latest content on business, relationships, music, spirituality, and book updates before anyone else.

You can also follow along on Twitter for more updates.

My promise: no spam, ever. Unsubscribe at any time.

Leave a Reply