The Dark Art Of How And When To Buy An Airline Ticket

Navigating the ever-more-complicated travel-reward cardsphere, frequent-flier programs, and Hawaiian stopovers, with help from 23 airline hackers.

- Ashlea Halpern

Buying a plane ticket has never been easier — or more complicated. Online travel agencies claim to offer the greatest fares; fare aggregators claim to offer the greatest selection of online travel agencies. Low-cost carriers promise to fly you to the moon for a pittance — but, oh, you want to check a bag and pick a seat too? That’ll be $100 extra. The legacy airlines want you to be loyal and book direct, but they’re constantly shifting the goalposts on miles hounds. Miles hounds, in turn, take to deep-dive hobbyist forums like FlyerTalk to rap in Klingon about their juiciest travel hacks. It’s all so dizzyingly complex you would be forgiven for wanting to punch your monitor every time you search for a flight. And that’s just the ticket purchase. As the recent United debacle illustrates, you can sift through hundreds of options, find a flight, book a ticket, board a plane, and still get dragged off, nose broken and glasses askew. This is not a dignified era in which to be an airline passenger, and the in-flight caste system is more acute than ever. But it’s not completely hopeless. We asked 23 airline experts to help us make sense of the contradictions: Is there really a best day to book? Are points more valuable than miles? What’s the best travel-reward credit card? And why does it seem like everyone and their broke cousin is flying business class except us? The experts did not agree on everything — some, for instance, still see the value in using online travel agencies like Expedia, while most others pooh-pooh them — although a deep love of Alaska Airlines was nearly unanimous.

Deal Hunters: Follow These Nerds

Why struggle through a torrent of airline promos when so many experts already make it their business to sniff out the best deals?

Secret Flying