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I Haven’t Paid for a Flight in Three Years Thanks to Credit Card Points

Yes, I’m gaming the credit card reward system. Here’s how you can too.

by Jenny Hart
Jan 11 2019, 3:52pm

Illustration by Kelsey Niziolek

When I was in high school, my father sat me down to teach me a very important lesson: “credit cards are evil.” I was confused; nearly every time our family of four went on vacation, at least a couple of our plane tickets were purchased with frequent flier miles. These miles were obtained not by flying frequently, but by my parents putting all of our household expenses on my dad’s trusty American Airlines credit card.

“But you get so much for free,” I protested.

“That’s how they get you," he said. "They lure you in with the promise of freebies, then bankrupt you when you don’t pay off your balance in time. Get a credit card as soon as you can to build up credit, but never carry a balance, no matter what. Never buy something you can’t afford.”

This scare tactic style of advice had some negative effects on my psyche: I struggled with severe money anxiety and became Depression-era frugal, tracking my spending down to the cent and keeping a three-ring binder of bank statements under my bed during high school. In college, I worked overnight shifts at my lousy on-campus job because it paid a dollar an hour more than during the day. Whenever I found myself in a situation where I had to unexpectedly spend—even if it was just a few bucks when out with friends—I would break out in a cold sweat, unable to focus on anything else.

But once I was out of school and in a job that finally paid me more than the minimum wage, I allowed myself to breathe and have a life changing realization: money exists to be spent, and when used responsibly, credit cards are amazing. By leaning in to credit lending industry, rather than being afraid of it, I discovered that I could earn a lot by spending very little. It’s easy to rack up points when you’re paying off a mortgage and for multiple dependents like my father, but what about the lone hand-to-mouth twentysomething? I found that with the right credit cards, my normal, daily expenses like buying groceries and gasoline could result in my traveling the world practically for free.

Jenny Hart Cards and Passport
Here are a few of my favorite credit cards.

Nearly every factor of travel can be purchased with points: flights are the most well known option, but hotel rooms, Airbnb stays, car rentals, and upgrades for all of the above are fair game, too. I know this because I’ve used points to book them all. I have a strong personal preference towards using my points for air travel, as that is often the most expensive part of a trip, so I will squirrel them away for that purpose. Thanks to my credit card points, it’s been several years since I’ve paid for anything beyond government taxes for a flight (which points do not usually cover).

I've flown everywhere from Milwaukee to Curaçao for free. In the past few months alone, I booked a round-trip flight from New York to Fort Lauderdale for 37,500 points on JetBlue (plus $11.20 in taxes, which I paid for with an airline credit I received from a past flight delay) and a round-trip flight from New York to Cancun for a mere 12,000 points on Delta (plus $85.42 in taxes, which I charged back to the same card). It was as easy—and sweet!—as pie.

Unfortunately, it may not be this easy for long—true to my father’s warnings, the credit card companies are not thrilled about our ability to make money off of them, and are brainstorming ways to curb it. If you’ve been thinking about trying your hand at credit card hacking, now is the time to do it, while you still can!

Here are some pointers to get you started:

Treat your credit card like a debit card

There’s an important truth to “don’t spend what you don’t have.” Points are only really valuable when they are earned for free, so whenever possible, I pretend that my credit card is a debit card that will shut off if the funds in my account are too low. In other words, if I don’t have the money in my checking account to cover something I would charge on a credit card, I don’t buy it. There are moments, of course, in life when having a line of credit is a lifesaver; but the second you find yourself paying interest or late fees, you’re no longer benefiting financially from using credit.

Charge EVERYTHING

It might seem silly to swipe your card for small purchases like your morning coffee, especially when you have cash, but those purchases add up—quickly. Every dollar spent is one, two, or even three or more points towards the ultimate goal of free travel. Save your dollar bills for shopping at small businesses with credit card minimums, and charge virtually everything else.

Scope out the best sign up bonuses

The most important factor in choosing a credit card is not the interest rate (we’re not paying interest, remember?), nor even the alluring promise of cash back. A credit card’s sign up bonus is the true bread and butter in collecting free miles. Many of the travel cards you’ll see advertised offer an average of 20,000 to 30,000 points to new members once a certain amount is spent in the first few months. This may seem like a lot (and it is!) but don’t settle for it—most of these same cards will have promotions throughout the year where that number bumps up to 50,000 points or more, which is often enough to fund a round-trip international flight. Choose which card to apply for based on how good that bonus is and keep an eye out for deals. Sites like CreditCards.com, CompareCards, NerdWallet and The Points Guy are great resources to follow to keep up on the best offers.

Plan ahead for big expenses

Part of the deal in earning a credit card’s sign up bonus is spending a certain amount of money in a certain amount of time. The standard amount you’ll see on most credit card applications is $1,000 over the course of 3 months. If you’re successful in charging the majority of your purchases (and live in a big, expensive city like me), this isn’t too difficult of a goal to hit. But oftentimes the better the sign up bonus, the steeper the required spending. The Chase Sapphire Preferred card, known pretty unanimously as one of the best travel cards out there, requires you spend $4,000 in 3 months to earn its 50,000 point bonus.

When I decided to finally apply for this card, I timed it around a period that I was going to be spending significantly more money than usual. In those 3 months, I invested in a new laptop and DSLR camera, and paid off the tuition for a class I’d recently enrolled in. I also asked my partner to let me put a few of his bigger expenses on my card, and had him Venmo me the value. By saving for a while and then making my big purchases all at once, I was able to easily hit the pricey spending requirement that I normally wouldn’t be able to afford.

Avoid paying an annual fee (or decide if it’s worth it)

In addition to interest and other fees, credit cards typically earn back the value of their free points by charging users an annual fee ($90 to 100 for most). But unless you are totally devoted to one card (I admit that I am to my Chase Sapphire Preferred), there is no need to pay this fee.

Some cards have zero fee. This is great, though they usually have small sign up bonuses. (For example, the JetBlue Card has a $0 annual fee, but you only get 10,000 points when you sign up. Meanwhile, the JetBlue Plus Card gives out 40,000 points, but costs $99.)

Out of the cards with good bonuses, you’ll see that about half of them waive the fee for the first year. Once you’re approved for a card, put a reminder in your calendar for 11.5 months from that date to cancel the card before it renews for another year and the fee hits your balance. As you’re getting ready to cancel your card, apply for a new one with a different airline and start the process again.

Depending on your situation, some annual fees are worth the points and perks. I happily paid a fee for one year of Hawaiian Airlines’ credit card, because I was awarded with 50,000 miles PLUS a one-time 50 percent off companion discount. In case you haven’t heard, flights to Hawaii are damn expensive. Scoring one and a half round-trip tickets for $99 total is a no-brainer.

Have frequent flier accounts with every airline

While many airlines preach the value of loyalty, it makes more sense for a budget traveler to cast a wide net and collect points from multiple airlines simultaneously, rather than focus on gaining “status” with one. Travel cards that are not affiliated with a specific airline (the American Express Gold Card, for example) allow you to redeem your points between multiple airlines by transferring them in 10,000 point increments, and many airlines have partnerships outside of credit cards that help you accrue points.

One example is Delta’s partnership with Lyft; when you link your Delta SkyMiles account to your Lyft app, you get 1 mile per dollar spent on rides (in addition to the points you get from the card being charged). Similarly, American Airlines has a dining program that gives you bonus AAdvantage points when you eat out at certain restaurants.

Be organized and responsible

The more credit cards and frequent flier accounts you open, the more you have to keep track of. Some airlines’ points expire, others don’t. Depending on when and where you fly, different airlines will have wildly different prices (in dollars and points alike). I keep a simple spreadsheet of all of my frequent flier account numbers and point balances, so I can easily access them when booking travel, and any time I have more than two credit cards open at once, I set up automatic payments to make sure I don’t accidentally become overdue. It’s a small hassle for a very big and rewarding result--seeing the world for cheap is beyond worth it!

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