The boarding procedure has barely started at Chicago O’Hare, and Ben Schlappig has already taken over the first-class cabin. Inside Cathay Pacific Flight 807 bound for Hong Kong, he’s passing out a couple of hundred dollars’ worth of designer chocolates to a small swarm of giggling flight attendants. The six suites in this leather-bound playpen of faux mahogany and fresh-cut flowers comprise the inner sanctum of commercial flight that few ever witness. They’re mostly empty now, save for two men in their twenties who seem even giddier than the flight attendants. The two stand to greet him. “This is so cool!” exclaims one, and soon Schlappig is ordering champagne for everyone.
This sort of thing happens to Schlappig nearly everywhere he goes. On this trip, his fans will witness Schlappig’s latest mission: a weekend jaunt that will slingshoot him across East Asia — Hong Kong, Jakarta, Tokyo — and back to New York, in 69 hours. He’ll rarely leave the airports, and when he does he’ll rest his head only in luxury hotels. With wide ears, Buddy Holly glasses and a shock of strawberry-blond hair, Schlappig resembles Ralphie from A Christmas Story if he’d grown up to become a J. Crew model. Back beyond the curtain in business class, a dozen jowly faces cast a stony gaze on the crescendos of laughter and spilled champagne — another spoiled trust-fund kid, they’ve judged, living off his parents’ largesse. But Schlappig has a job. This is his job.
Schlappig, 25, is one of the biggest stars among an elite group of obsessive flyers whose mission is to outwit the airlines. They’re self-styled competitors with a singular objective: fly for free, as much as they can, without getting caught. In the past 20 years, the Internet has drawn together this strange band of savants with an odd mix of skills: the digital talent of a code writer, a lawyer’s love affair with fine print, and a passion for airline bureaucracy. It’s a whirring hive mind of IT whizzes, stats majors, aviation nerds and everyone else you knew who skipped the prom.
Schlappig owes his small slice of fame to his blog “One Mile at a Time,” a diary of a young man living the life of the world’s most implausible airline ad. Posting as often as six times a day, he metes out meticulous counsel on the art of travel hacking — known in this world as the Hobby. It’s not simply how-to tips that draw his fans, it’s the vicarious thrill of Schlappig’s nonstop-luxury life — one recent flight with a personal shower and butler service, or the time Schlappig was chauffeured across a tarmac in a Porsche. But his fans aren’t just travel readers — they’re gamers, and Schlappig is teaching them how to win.