From the patio of an overwater bungalow in Maldives, the turquoise Indian Ocean waters behind them, Seattleites Kaelee and Brian Chang made an Instagram video describing how they got their dreamy tropical vacation for free. In the clip, Brian explains how he put most of their wedding on a new Chase Sapphire Reserve Card, and how Kaelee's Marriott Bonvoy credit card could convert valuable points into that luxury Maldives room. A complicated dance of signup bonuses and transfers and quadruple-point-deals led to a nearly free once-in-a-lifetime vacation.

Zach Griff recognizes that kind of accomplishment. "Free travel, whether it's by points or miles, is so alluring," he says. He's a senior reporter at the Points Guy, a whole publication devoted to the rewards programs that dominate recreational travel. The website grew into its current size about decade ago, which is about when Griff figures the trend proliferated.

Frequent flier programs have been around since the late 1970s, when regional airlines debuted the system; American Airlines' version, still active today, debuted in 1981. The idea was to reward frequent customers with occasional freebies, logging them per mile flown, and earn loyalty. Co-branded credit cards emerged in the 1980s, eventually leading to the point system, where dollars spent translate into hotels and flights obtained through specialized web portals.

Today, says Griff, people put all sorts of purchases on a credit card to rack up points—not just weddings but property taxes, college tuitions, even mortgage payments. In return, those cards will come with point rewards as well as perks like reimbursement for TSA Precheck or Clear, or airport lounge access.

But to come out ahead, says Griff, "one of the golden rules of this game is that you have to pay your cards on time." These companies shell out the gifts because they expect to make a lot back in interest charges from people who don't. "The minute you start accruing interest, any upside is diminished.”

While early versions of mileage plans kept the user siloed in one brand—earn on American, use on American—these days airline partnerships allow for broader use; credit card points often go even wider, to be used on any flight. Many mileage programs have introduced companion fare passes, letting their branded credit card users add a second seat to a reservation for a low price. For years, this was the biggest perk Alaska Airlines offered with its card. But even those are changing; in 2023, Alaska  began requiring new cardholders to spend a certain amount on their cards—now $6,000 a year—to earn the perk.

Frequent flier programs used to be a lot more based in business travel; think George Clooney's character gunning for membership in an elite 10 million mile club in the movie Up in the Air. But today they're for everyone—just try to split a meal in Seattle and you'll see Alaska Airlines Visa cards pile up when the check comes.

That means that the value of miles and points has changed, Griff says. "More and more people are using them and the demand of flights has outstripped supply." Alaska reformatted their award plan for 2024, largely changing how many miles it takes to get a freebie; Griff calls Alaska's value "diminished," though his the Points Guy colleagues labeled the shift "a mixed bag." 

Across the board, the evolution of mileage plans has put things like lounge access and upgrades into higher, harder-to-reach tiers, and often changing accrual to be more about money spent than distance traveled. Anything can be turned into a commodity: free checked bags, lounge access, boarding group. "Airline status is a hamster wheel for many people. Once they get on it it's very hard to get off," says Griff.

And these days there's another class of free traveler hopping the globe, the influencer. These very online content makers create the kind of marketing content that used to be done by agencies. When approached for freebies, hotels and travel companies often ask for rigorous accounting of their social media audience before they foot the bill.

But Kaelee and Brian Chang are not really influencers, just self-described "normal people" who made their video when friends kept asking how they scored such a great trip. Still, they're particularly savvy normal people. Food on their Maldives trip couldn't be purchased with points, so they filled up on smoothies at lunch and put meals on Kaelee's Marriott credit card. Every dollar they spent on pandan muffins and rambutan fruit earned 17x points on that account—ready to be used on another dream vacation.