Travel for Free: Secret Ways to Earn a Ton of Miles

Bonnin Studio/Stocksy)

Billie Cohen - Getting something for free is one of the best things in life — and in travel. That’s a big reason frequent travelers join loyalty programs: Rack up enough miles and points and you could score a free upgrade, hotel stay, or flight. So how do you get there? The path to free travel is paved with credit cards; they are the easiest way to begin collecting points, frequently delivering a hefty number of miles as a sign-up bonus or offering ongoing rewards via certain types of purchases. The initial bonus varies depending on what card you get and what airline or hotel chain you want to commit to, but there are many options to choose from — and many experts who can keep you up to date on the best ones. One of those experts is Gary Leff. Author of the extremely-popular-in-this-world View from the Wing blog, Leff is one of the best informed and most respected miles junkies around. In addition to reporting on the top deals and convoluted intricacies of loyalty programs, Leff also runs Book Your Award, a company you can hire to redeem the best possible business- or first-class award tickets for your miles. Short story: This guy knows points. In fact, he regularly earns enough that he travels for free: to the Maldives every year for the past five years, to Australia twice this year, and once to Barcelona just to have dinner at El Bulli, back when that famed restaurant was open.

Now it’s your turn. Once you have your preferred credit card in mind (and Leff has suggestions for that too), you can really start rolling in the rewards by following these secret steps:

1.  Start out with a big bonus

“There’s one broadly accessible credit card right now offering a 100,000 bonus: the British Airways Visa Signature from Chase, though the spending requirement for the full bonus is significant,” Leff says. You only get all 100k Avios once you’ve spent $22,000 total ($2,000 in the first three months of opening an account, then another $20,000 within your first year).

2. Pay your bills 


Earn miles for things you do anyway: like paying your bills. (Photo: iStock/DNY59)

“Set up an account with Plastiq.com and you can pay any bill you want with a credit card — even if the recipient doesn’t usually accept credit cards. Plastiq.com mails out a check for you and then bills your card. The company takes a fee of 2.5 percent on top of every transaction, but this way you can earn miles by paying your rent or mortgage, for instance, or your car payment… at a cost (though they frequently run specials at lower cost).”

Related: The Best Rewards Credit Cards for Travel

3.  Get your bank to give you points

Invest in your travels while you invest in your future. Leff points out: “You can earn up to 50,000 AmericanDelta, or United miles opening and funding a Fidelity investment account.”

4. Get your bank to give you more points

“I earn American Airlines miles each month via my BankDirect checking account. There’s a signup bonus of up to 22,000 miles. They give me 100 miles for every $1,000 average balance each month. Since I wind up with lots of business reimbursements, my checking balances tends to be high and I’ve earned as many as 50,000 miles in a year.”

5.  Shop online


Shopping online could add up to travel rewards. (Photo: Bonnin Studio/Stocksy)

“Online shopping is always a big one,” Leff says. So if you’re going to be shopping anyway, you might as well get some extra rewards out of it. Check with your credit card’s online shopping portal to learn where you can earn points for every dollar you spend, and look for specials when you’ll earn even more points per dollar than usual. “Often the miles per purchase are small,” Leff notes, “but people earn a ton of miles buying things online through a shopping portal and then selling the items to recoup their cost.” He adds that this practice of “re-selling” has pros and cons — one of which is the possibility that you won’t be able to unload the merchandise you bought, leaving you with a pile of stuff you don’t need and without the cash that you do. Buyer beware.

Related: 10 Dirty Little Secrets of Frequent Flier Programs

6. Do good 

Here’s one you can feel good about: “Do good work by making Kiva loans to support economic development around the world…and earn miles,” Leff says. Kiva is a nonprofit organization through which you can lend small amounts of money to micro-entrepreneurs in countries across the globe. For example, with as little as $25, you can contribute to a woman in Lebanon who’s opening a school for special-needs students, to a man in Bolivia who is starting his own bee-keeping business, or an entrepreneurial woman in Ecuador who wants to purchase a dairy cow. “Charge your Kiva loans to a credit card and earn miles,” Leff explains. “Once the loans are repaid you can withdraw the funds back to your bank account. Kiva has a remarkably high repayment rate.” And while it can take a while to make your money back (and there’s always the chance that you won’t), the personal rewards here go way beyond miles and hotel stays.

7. Sign up for promotions

Check the websites or brochures for any loyalty program you belong to—many offer special promotions with various partners, like spending money at a shop, or participating in an online event. Over the years, Leff has found several interesting ones: “I’ve earned free flights from AirTran (later acquired by Southwest) for dumpster diving soda cups at Wendy’s, and I’ve earned Delta miles for a hair-replacement consultation (I have a full head of hair),” he says. He adds that you should also be on the lookout for short-term promotions, which often require registration. “Register for the offers,” he advises, “It’s free, and you just may wind up with extra miles.”

Related: How This Guy Travels the World for Free

8. Dine out, smarter


Let any card help you earn miles when you dine out. (Photo: iStock)

Some credit cards enable you to earn you points when you dine out, but the Rewards Network lets you earn them no matter what’s in your wallet. Membership is free; simply register a credit card on the website and choose what kind of reward you want: airline miles, hotel points, money-saving discounts, or contributions to nonprofit organizations. Then when you use that card at one of the 11,000 restaurants, bars, and clubs in the network, you’ll start to rack up rewards. “It’s worth signing up for the program, I often earn miles without even realizing that a restaurant participates,” Leff says. “This is great for eating with groups and collecting the cash from friends, or picking out a participating restaurant for a reimbursable business meal.”

9. Once you earn them, don’t lose them

If you’re racking up loyalty points or miles from several sources, it can be tricky to keep track of them all. For that, Leff suggests Award Wallet. “It not only lets you update account balances on a single screen and log into accounts with a single click, it can help track accounts to prevent miles from expiring,” he explains. Technically, Award Wallet doesn’t help you earn miles or points, but it does help keep you from losing them, which, Leff notes, “is kind of like earning them.”

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