How I Got Myself a Bunch of Free Flights to Awesome Places.

by Dan Oshinsky on March 11, 2012

At the end of 2012 2011, I made a promise to include travel on my list of things for the upcoming year. Except that I’m not sitting on a mountain of disposable income here. If I was going to travel, I was going to do it cheap.

So that’s how I got interested in travel hacking.

Travel hacking is this movement of people who rack up frequent flier miles in all sorts of ways. Most consumers think frequent flier miles are just for those who fly a lot. That’s wrong. These days, you can earn just as many miles on the ground as you can in the air. Buy music on iTunes? You can earn miles. Subscribe to Netflix? You can earn miles. Buying flowers for your girlfriend? Yeah, you earn miles.

Point is: I started tapping into the travel hacking world back in December. Since, I’ve paid attention to how I spend and how it helps me earn miles. I’ve learned way more about how credit works.

This is the especially cool part: I’ve got 200k+ miles sitting in my frequent flier accounts right now. I’m not broke, and my credit doesn’t suck. And best yet: Whenever I find myself the time to take vacation, I’ll be flying for free.

So here’s what I’d suggest for you, Potentially Curious Travel Hacker of Tomorrow:

1. Set your goals

If you could go anywhere in the world, where would you go? I’d really like, in the next 18-24 months, to see New Zealand and Croatia. It’ll take 100k to get to New Zealand, and 40-60k to get to Europe.

If you’re curious about how many miles it’ll take to get to your dream destination, here are the mileage reward charts for the SkyTeam (including Delta, KLM, Air France), Star Alliance (United, USAir, Lufthansa, Swiss Air, Air New Zealand, Air China, Air Canada), and Oneworld alliances (American, British Air, Cathay Pacific, Iberia, Japan Airlines, LAN, Qantas)(1).

2. Sign up for AwardWallet

AwardWallet is this incredible site that keeps track of all your frequent flier miles from all the airlines, hotels, and rental car companies you use.(2) They’ll automatically tell you when you’ve earned miles, and they’ll tell you when your miles are about to expire. (And it’s free!)

If you’ve flown at all in the past 24 months, you’ll see miles show up on your statement. Thanks to AwardWallet, I found out, quite accidentally, that I’d already racked up 50,000 miles on United. That’s two free domestic round trip flights. I had no idea I’d been sitting on that gold mine.

Sign up and start tracking your miles.

3. Start following these guys on Twitter

@MilMileSecrets
@thepointsguy
@boardingarea
@FlyerTalk
@HackMyTrip
@FrequentMiler
@milepoint
@FrugalTravelGuy
@airfarewatchdog

They’re tapped into the world of miles and deals, and they’re blogging about deals and offers. Like, a couple of weeks ago, British Airways had a crazy deal: For every dollar spent, I’d earn 36 miles on BA. I had to grab some gifts anyway for family, so I pulled out the credit card and spent a few hundred bucks. Now I’m sitting on a roundtrip flight on BA(3).

That’s what travel hacking is all about: Spending money on things you want/need and getting something else in return: Miles.

To get a free domestic ticket on any of the big American airlines — American, Delta, United — you need about 25,000 miles. That’s what you’re shooting for.

If you’re looking to dive into the deep end with travel hacking, consider joining the Travel Hacking Cartel. I did back in January. It costs a few bucks each month, but they send me a few awesome deals each week(4). They’ve also got all sorts of tutorials about how to redeem miles.

4. Start spending… small

You can get miles for everything these days. All it takes is a handful of small purchases. Like:

A. Airline dining programs

Airlines have deals with some restaurants and bars. You register your credit/debit card with the program, and when you use it to buy food/drink, you automatically earn miles.

For example, I’m a member of United’s dining program, and at certain places here in Columbia, MO, I get 3 miles for every dollar spent. When I buy a sandwich at Which Wich, I earn miles. Same if I buy a beer at Room 38. Or Quintons. Or Bleu. Or Boone Tavern.

American Airlines, Delta, Southwest and US Airways all have dining programs, too.

If you’re in a different city, pull out the credit card. Last month, I bought some drinks(5) at a bar in NYC. I got an email later that week that the place was a United dining partner, and I’d been credited with 200 miles. Sweet!

This alone won’t get you that flight to Tahiti. But it’s an easy way to earn miles on things you’re already buying.

B. Shopping online

Same goes for online purchases. You can get 1 mile per every dollar spent on Apple products, and 3 miles for every dollar spent on iTunes. Like J. Crew? On American, you can get 5 miles per every dollar spent on that new sweater. Sign up for Netflix, and United will give you 1,000 miles. Buy flowers on FTD, and you’ll get anywhere from 20 to 36 miles per dollar spent.

Don’t believe me? Search here for your favorite retailer. All you have to do is log into the specific airline’s shopping store before going to, say, JCrew.com, and you’ll earn the miles.

5. Sign up for a credit card (if you can)

Here’s the precursor to this: If used incorrectly, credit cards can cause you trouble. Credit card debt can keep you from doing things like buying a home, or a car, or pretty much anything where real money is at stake.

So here’s my brief advice: If you don’t have money to spend, don’t go getting credit cards. You will spend money you don’t have, and you will end up in debt.

But if you have money to spend, credit cards are an excellent way to rack up miles. Some cards come with a big sign-up bonus. Some give you a bonus after a minimum spend. Some give you perks — free airline lounge access, free checked bags.

This site has more advice on which cards are right for you. You’ll want to pick one (or three) that fit your travel needs/wants/dreams.

What Now?

Maybe travel hacking isn’t for you. Maybe you’ve got a cash-back debit card, and you’re happy with it. Nothing wrong with that.

But if you love to travel, I’m telling you that there’s a way to make it happen. Like Ferris once said:

If you have the means, I highly recommend checking it out.

  1. Independent airlines like Southwest and AirTran have their own frequent flier programs, and they’re both totally different. Check them out for yourself if you fly either of those with frequency.
  2. The one catch: American Airlines blocks the site. But everybody else in the universe works on AwardWallet.
  3. To clarify: BA’s miles program is different then most. A short flight — say, NYC to Toronto — starts at 4,500 miles. I’ve got 11,000+ miles on BA now. So it’s a roundtrip, but nothing long-distance.
  4. 1,000 points for signing up for — and then immediately canceling — text messages from Hilton? Thanks, Travel Hacking Cartel!
  5. Okay, “some” might be an understatement here.