Up in the Air: Meet the Man Who Flies Around the World for Free

He’s treated equally well by flight attendants, who are among his rowdiest fans. When a chief steward recognized him on one superluxury carrier, Schlappig stepped into his onboard shower to find a bottle of Dom Pérignon on ice waiting for him. On a recent international flight, an attendant maneuvered an unwitting Schlappig into an empty row, administering what he delicately terms a surprising and unwanted hand job. (“It was a disaster,” he says. “I tried to get out, but there was no point.”)

Despite his success, many in the Hobby think the days of hopscotching across the globe are numbered. Paranoia is the lingua franca of all Hobbyists, and now is a good time to be pessimistic. Earlier this year, Delta and United both switched to revenue-based reward systems: Frequent-flyer miles are now awarded by total dollars spent, effectively ending the practice of mileage running. Schlappig seems unconcerned. “I’ve been at this for 10 years,” he says. “And there’s not a single year where I didn’t hear at one point or another, ‘This is coming to an end.’ But every year, we find new opportunities. We’re one step ahead of them.”

For some, the game has evolved from a wonkish pastime into an ends-justified obsession with beating the airlines — less Rain Man, more Ocean’s Eleven. While the game’s traditional methods remain technically legal, these Hobbyists — imagine them as the Deep Web of the Hobby — use tactics that routinely violate airline terms and conditions, techniques that can span a gradient from clever and harmless to borderline theft. (Schlappig concedes that he pushes the rules but insists he is careful not to break any laws.) Take the practice of “hidden-city ticketing” — booking your layover as your final destination, like buying a ticket from Point A to Point C, then sneaking away at B — or “fuel dumping,” a booking technique that confuses the price algorithm to deduct the cost of fuel from a ticket, often at an enormous discount. In this strange and risky world, black markets exist where brokers buy and sell miles, and Hobbyists pay others to fly in their names.

They also write custom code to hunt the Web for “mistake fares” posted accidentally by airlines and hotels. “My friend can write one of these scripts in two hours,” one Hobbyist tells me. “These are huge companies, and they don’t write a simple code to double-check their prices. It blows me away.” He recently used a custom script to book a Westin presidential suite for $10.