The Secret To Earning And Spending Credit Card Points For Travel, According To A Guy With 12 Million Airline Miles

The world of credit card points has always felt a bit like trigonometry to me — you know that mastering it is possible, but is it really worth all the work?

Enter Chris Hutchins, a guy who gets a kick out of flying first class for free — and does it often. In fact, he’s so serious about hacking life that he started All the Hacks, a chart-topping podcast where he shares his secrets. 

I was lucky enough to chat with Hutchins and ask him what felt like a million questions on credit card points and travel. THANK YOU, CHRIS.

Before you pick a credit card, you need to determine the areas where you tend to spend the most money. Gas? Groceries? Flights? 

“Mint [a budgeting app] or your credit card company will show you where you spend your money,” said Hutchins. Once you know what areas you spend the most, you can find a credit card that rewards you for making those purchases. 

The credit cards Hutchins recommends for people who are interested in accumulating points are listed below. (It’s worth noting that this is just general advice — everyone is different.)

– Citi Premier gives you 3 points for every dollar spent on restaurants, supermarkets, gas stations, air travel, and hotels. 

– Chase Sapphire Preferred gives you 3 points on dining and restaurants worldwide and online grocery shopping and 2 points on all other travel. 

– Capital One Venture gives you 2 miles for every dollar spent on anything.

– Bilt gives you 1 point for every dollar you spent on rent (yep, that’s right), plus 2 points on travel and 3 points on dining.  

One way to accumulate points fast is to choose a card with a nice signup bonus. For example, you might get a free flight just by signing up for a card (you typically have to spend a certain amount of money in the first few months to get the point bonus).

This is part of why Hutchins has accumulated so many credit cards. “I was never the person opening up 15 to 20 cards a year, but I was the person who anytime I saw a card with a100,000 or 80,000 point bonus, I’d sign up,” he said.

Accumulating credit card points the way Hutchins does is not something most people have time for or an interest in. But, if you’re curious (like I was), he says these “are probably the three cards I use the most, in fact of the 14, these are the cards I use for almost all of my spending.” 

– AMEX Gold, which gives 4 points per dollar spent at supermarkets and restaurants

– Chase Sapphire Reserve, which gives 3 points per dollar spent on travel and dining

– Capital One Venture X, which is the catch-all card that gives 2 points per dollar spent on everything and anything

Hutchins uses his other 11 cards for rare one-off purchases that make sense. For example, he says it’s smart to use the Marriott Bonvoy credit cards, which give you up to 6 points for every dollar spent, at hotels participating in Marriott Bonvoy.

When Hutchins first got into the credit card game, this was his main method — and it worked like a charm. 

“Every time we went to dinner, I offered to pick up the tab, and people would give me cash,” he said. “Every time I had the opportunity to put something on my card, I would.”

Then, he started organizing group trips and events just so he could put the charges on his credit card. “Once all my friends started getting married or getting engaged, I’d plan all the bachelor parties. … People would send me the money, and I’d book all the stuff. I’d end up putting 15 flights on a credit card to New Orleans,” he said.

As you can imagine, deciding what card to use for what purchases can be tricky. When you’re not sure, Hutchins recommends using the CardPointers app. The app will tell you which of your cards will give you the best reward for various purchases. 

“They are not linking to your bank account, they are not learning how you spend money,” Hutchins explained. “They’ll just tell you for common categories [like flights or gas] and for all the cards you have, these are the best for spending.”

One of the biggest perks of going with a credit card from Chase, Capital One, Amex, or Citi is that you can transfer your points to any of their transfer partners. (For more, re-read #4.)

But the trick can be deciding if you should transfer the points to Delta or United. Hutchins uses Point.me for this cumbersome task. “They’ll go search all 30 airline websites, and you can tell them what points you have, and they’ll tell you where to transfer points,” he explained, noting that the site charges $5 for a day pass and has annual memberships.

Airlines put aside a certain number of reward seats for each flight, but the trick is finding and securing these rewards seats when they’re still a good deal. 

“There’s not a hard and fast rule, but I’d say planning a trip as far out as possible or as short as possible are your best options,” he said. And as you might guess, flexibility is key. “The more flexibility you have either on when you go, where you go, or how far in advance you plan, the more confident I am that you’ll find an incredible deal. … If you’re flexible, it will almost always work out.”

In general, he sticks to the “one penny a mile rule,” so, for a $1,000 flight, you need to find a reward seat that is100,000 points or less, or it doesn’t make sense.

It can be tempting to use your points for that weekend car rental or to offset the cost of your hotel, but Hutchins says redeeming points for cars, upgrades, and hotels is almost never worth it. 

“Using miles and points that are not part of a rental car program to rent a car is almost never a good deal,” he explained, noting that “On the whole, airline points are worth a lot more than hotel points.”

He says that if you have flexible points (points earned via a bank card, not an airline card), the “best value comes out of booking international flights and Hyatt hotels.”

The perks you might get from opening credit cards, racking up charges, and transferring points is never worth it if you can’t pay your credit card off in full each month.

“None of this applies to anyone who isn’t able to pay their cards off in full every month — so, no amount of interest is worth the perks,” Hutchins said.