Since I posted my recent article How I Afford Travel: Badass Trips On A Not-So-Badass Budget, I’ve received a lot of questions asking me to go into more specifics. I started learning how to do this a few years ago, and since then I’ve successfully taken several international flights that were paid for almost entirely by frequent flyer miles – miles I earned without stepping foot on an airplane. My friends, this little-known, totally legal game is called travel hacking. And I’m happy to share specifics with you – I’ll even share details of my most recent trip, explaining exactly how I did it and how much I paid for my flights.

But before we dive into this, we should identify your travel goals.

Ask yourself: Do you already know where you want to go? Or can you be flexible?

See, there are ultimately 2 ways to approach earning and redeeming miles for free flights.

Strategy 1: Decide where you want to go, and plan accordingly.

Certain airlines are better for certain destinations, and the valuation of miles can vary widely from airline to airline. If you know where you want to go, you can review award charts, award maps, and redemption rates to figure out which airline will give you the best deal. Most airlines are part of an alliance, meaning you can redeem one airline’s miles for flights on another – for example, you can redeem British Airways miles for American Airlines flights because they’re both part of the OneWorld Alliance. Once you know which airline – or which airline alliance – will get you to your preferred destination for the lowest number of miles, you can keep an eye out for valuable cards from those frequent flyer programs (I’ll explain how to find these cards in a few).

Strategy 2:  If you’re open-minded, find the best offers and figure out where to go later.

This method is all about choosing the credit card offer that gives you the best sign-up bonus and points per dollar spent, and is part of an alliance that gives you plenty of options – then stockpiling the miles for your future mystery trip. When it’s time to plan your trip, have several options in mind and choose the one that costs the least amount of points. Disclaimer: This doesn’t work if later on you don’t want to be flexible (I’ll tell you how this happened to me in a bit).

But, keep in mind there are more ways to earn miles than credit cards.

Everyday online shopping. Many airlines have online shopping malls that allow you to earn miles per dollar spent. You simply login to your account, find the store you want to purchase online from, and click through to that store’s website. Tracking cookies will do the rest.  With everything from Walmart, Sears, Kohl’s, and Sephora to higher-end department stores, there are tons of ways to funnel everyday online purchases through an airline’s shopping mall to passively earn tons of miles without ever getting on an airplane. It’s so easy it’s stupid.

EVReward.com. This site is basically Google for shopping rewards. Just type in which store you want to shop and it’ll tell you which reward programs you can use to earn points or miles there.

Travel hacking comes with huge benefits – and I’m not just talking about free flights.

Free stopovers means you can see more places.

When you book reward flights, you can strategically add a stopover for free – and then stay at that stopover location for several days, thereby adding another destination to your trip. When I went to Jordan, Egypt, and Spain, my original flight was from JFK to Sharm El Sheikh (where I went scuba diving in the Red Sea) with a stopover in Amman, which I used as a base when exploring Petra, Jerash, and the Dead Sea. But my return flight was from Cairo to JFK, with a stopover in Madrid. All I had to do was get from Sharm El Sheikh to Cairo, which was a very cheap in-country flight I purchased separately.

You can do this with many airlines. They value your flight from point A (in this case, Cairo) to point B (JFK), and if there is a combination of flights that routes you with a stopover in an amazing location, so be it. It’s your job to research those flights on the airline’s website to find the ones you really want – your stopover will probably have to be in a hub city. Notice also that my roundtrip reward flight included flying to and returning from different cities – I didn’t have to make it back to Sharm to fly home. That flexibility, called Open Jaw, is another benefit of reward flights.

You’re more likely to see places you otherwise might never have.

All of this means you’re opening yourself up to more options than you’d have with a paid flight. If it’s just as easy to fly home from a different city than the one you arrived in, and if it’s cheap to get from that city to the other, why wouldn’t you? And if you’re going with Strategy 2, valuing flexibility over any one destination, when it comes time to book a trip, you wind up researching a variety of amazing trips to see which one makes the most sense – which can lead to some off-the-beaten path places. I’m admittedly something of a Europhile and I’d been dying to go back to Italy since I studied abroad there 7 years ago. Do you think I was itching to get to the Middle East first? No, but the opportunity to visit a part of the world I may never get the chance to again (considering the tumultuous political climate) was too good to pass up. I let flexibility and opportunity take the reigns, and had an amazing experience I’ll never forget.

And you know what? I still made it to Italy on miles the next year. In fact, I’ll use that trip to give you another example of how you can use miles to book flights in creative ways - and I’ll even tell you exactly how much I paid for each flight.

Itinerary: Germany, Italy, Croatia, and Spain

(Yep, Spain again. Did I mention I’m also a bit of Spanophile?)

Here’s how it worked:

Flight 1: DFW to ORD (Chicago) - Spirit Airlines - $118.89.

The best mileage deal that got us to Europe was from ORD to Berlin. I could have also used British Airways miles to get from DFW to Chicago, but it seemed more prudent to save those and shell out for a cheap flight to ORD. It was still significantly cheaper than if we’d purchased the RT US-to-Europe ticket outright. Most international flights leave in the evening, so we had all day to get to ORD. Easy.

Flight 2: ORD (Chicago) to Berlin - AirBerlin 25,000 miles and a $2.50 mileage surcharge fee.

Mileage surcharges are fees that airlines charge in addition to the miles you’re redeeming. They can vary depending on how many miles you want to use, and the airline’s policies.  However, sometimes airlines charge much more – like British Airways, in this case.

We weren’t initially planning to go to Germany on this trip. We were concerned primarily with going to Italy and Croatia (in this case we were being a little less flexible – we were dead set on going to Italy and Croatia but the flights weren’t working out perfectly). However, British Airways charged $300+ in mileage surcharges to get us to Europe on BA and most of their OneWorld partners, but for some reason only $2.50 on AirBerlin – but the catch was we had to fly into Berlin. Inter-European flights are so cheap that it was financially more viable to fly into Berlin, then immediately fly to Florence on another ticket.  In this case we decided to stay one night in Berlin, but we could have had just a short layover at the airport before heading to Florence if we preferred.

Flight 3: Berlin to Florence. Vueling, paid 92.42 Euros (approx. US $125).

Vueling had the cheapest airfare from Berlin to Florence. Note that we researched the cost of both this and the Spirit flight that got us to Chicago before ever booking our reward flights, to make sure it all still worked out financially in our favor.

Flight 4: Rome to Dubrovnik - Croatia Airlines, paid 1,581 Croatian Kuna (approx US $282).

We agonized over how to get from Italy to Croatia. Despite being just a short crossing of the Adriatic, the flights were quite expensive. Though we could have taken a bus or an overnight ferry, we made a decision to value our time over our money, biting the bullet and taking the Rome-Dubrovnik flight.

It cost almost $300 per person – not ideal. But the story behind this flight is somewhat interesting: though we only needed a one-way, the flight we booked was actually a round trip. Several months later, a flight left from Zagreb for London with our names on the roster, but our butts back home in Dallas. It’s ridiculous that it was cheaper to book a round trip flight that included destinations we had no intention of visiting than it was to simply book a one-way, but that’s the weird, irrational nature of airline pricing.

Flight 5: Dubrovnik to Barcelona - Vueling, paid 98.24 Euros (approx. US $134).

We found good options out of Barcelona, so we decided to tack that onto our trip. Barcelona is one of my favorite cities in the world, so of course I jumped at the chance to spend a few days there at the end of our trip. We paid $134 each for this Vueling flight.

Flight 6: BCN (Barcelona) to DFW - 30,000 miles and a $49.98 mileage surcharge fee.

We actually could have flown out of either Barcelona or Paris for the same amount of miles + fees, but we opted for Barcelona. Fortunately, our itinerary got us back to DFW, through Miami, without having to fork a few more dollars over to Spirit. 

So, in the end, this was actually sort of an expensive trip for a travel hacker, just considering flights alone (although we did take 6 of them!). Keep in mind, the flights to and from Europe were only $171.37 (that’s including the paid Spirit flight to get to ORD)! We then spent $541 on inter-European flights (paid with cash, not miles), which was unusually high for us. This is because we went with Strategy 2 – originally accruing miles not knowing everywhere we’d want to go, and then being pretty specific about destinations after the fact. If we’d been less picky about going to Croatia, or willing to travel more slowly within Europe, we could have spent a lot less money. 

Hopefully this helps illustrate how you can creatively use reward flights to travel in ways that are not only more cost effective but also more interesting.

If you want more information on how to do this yourself, you’ll need some good resources to get you started.

As I mentioned in How I Afford Travel, I learned the basics in 2010 from Frequent Flyer Master by Chris Guillebeau. Hundreds of thousands of miles earned and several international trips later, I still think it’s the best, most comprehensive, yet least intimidating guide for those who are totally new to this. My best advice to anyone looking to get started as a travel hacker is to pick up Frequent Flyer Master, print that sucker out and dive in.

You can also check out the blogs of well-known travel hackers, including ThePointsGuy.com, FrugalTravelGuy.com, and forums like FlyerTalk.com to get more information.

How to find the best reward credit cards:

Several people have asked if the Frequent Flyer Master covers specific credit cards. Yes, in addition to teaching you about all the different tactics, tricks, and strategies for earning and redeeming miles, it will tell you about the best overall credit cards for travelers. But the more rare bonus offers – like the one that earned me 100,000 British Airways miles – will come and go more quickly. They’re not always advertised by credit card companies, and the best deals only last for a few hours. So how do you find out about them?

There are two options:

1. Know where to look and do the research.There are a couple of mileage bloggers who write about credit card offers, including FrugalTravelGuy.com. The most up-to-date information is on Flyertalk.com, which is where all the pro travel hackers hang out and trade secrets.

2. Take the lazy/busy person’s route.It’s a lot of work to keep up with this stuff. If you’re not up for it, you can instead be alerted to new reward deals as they happen with a notification service like Travel Hacking Cartel. This was started by the same travel hacker who created Frequent Flyer Master. His team of travel hacking experts research new deals (including mistake fares) constantly, alerting you in real time. It’s a paid service — it’ll run you $15 per month — but he guarantees you’ll earn 4 free plane tickets per year.

Not from the United States? As you might have figured out, most of the info out there is for Americans, so you’re probably having a hard time finding information on reward programs for everyone else. Well, about half of the Deal Alerts in the Travel Hacking Cartel are for non-US citizens. I personally don’t know of any other service that alerts you to non-US deals, so if you’re from elsewhere in this great big world and serious about travel hacking, this might be worth checking out.

So there you have it. This is my honest advice for anyone interested in playing the travel hacking and reward credit card game. This whole travel hacking thing can seem intimidating at first, but with a little research and willingness to learn, you can be on your way to the trip of a lifetime for next to nothing. Trust me – it is definitely worth it.

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Luxor, Egypt. 2012