The Dark Art of How (and When) to Buy an Airline Ticket – Ashlea Halpern May 18, 2017 8:00 am


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Photo: Color treatment by Gluekit

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 airline 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.

Meet the Experts

Melinda Danielsen, author of Magic of Miles // Daraius Dubash and Emily Jablon, co-founders of Million Mile Secrets // Chris Guillebeau, founder of the Travel Hacking Cartel // George Hobica, founder of Airfarewatchdog // Roman Kalyakin and Vladislav Protasov, co-founders of Flystein // Scott Keyes, founder of Scott’s Cheap Flights // Matthew Klint, co-founder of Award Expert and author of Live and Let’s Fly // Stefan Krasowski, author of Rapid Travel Chai // Dan Lack and Leigh Rowan, co-founders of Savanti Travel // Jamie Larounis, founder of the Forward Cabin and co-founder of Frequent Traveler University // Matthew Ma, co-founder ofthe Flight Deal // Scott Mackenzie, editor of Travel Codex // Seth Miller, aviation journalist and founder of Wandering Aramean // Adam Morvitz, founder and CEO of Juicy Miles and author of Point Me to the Plane // Ben Schlappig, founder of One Mile at a Time // Roman Shteyn, co-founder and CEO of Reward Expert // Brett Snyder, president of Cranky Concierge Air Travel Assistance // Todd Sullivan, co-founder of Flightfox // Tarik, founder of Secret Flying // Aktarer Zaman, founder and CEO of Skiplagged

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
Good for: Flash sales, last-minute deals, and crazy-low error fares.
Recent score: Round-trip economy fare from New York to Navegantes, Brazil, for $479 on Avianca.

The Flight Deal
Good for: Strategies to help maximize your miles, plus notifications of deals and error fares. (To make the cut, a deal must cost 6 cents or less per mile.)
Recent score: One-way economy fare from New York to 11 European cities (including Barcelona and Paris) starting at $145 on TAP Portugal.

Scott’s Cheap Flights
Good for: Deal alerts on cheap international flights. Subscribers to the free newsletter get a third of Scott’s deal notifications; premium subscribers ($39 a year) receive everything, plus ad-free alerts customizable by departure airport.
Recent score: Round-trip economy fare from New York to Tel Aviv for $538 on Air Canada.

Airfarewatchdog
Good for: Points/miles minutiae, fare alerts customizable by route, and a daily roundup of the internet’s top-50 deals.
Recent score: Round-trip economy fare from New York to Mexico City for $217 on Volaris.

The Points Guy
Good for: Miles and points strategies, airfare alerts, credit-card news, guides to loyalty programs, and candid airline reviews. (Founder-CEO Brian Kelly is very particular when it comes to business and first-class-cabin offerings.)
Recent score: Round-trip economy fare for two people from Newark to Athens for $975 on Emirates.

Notable Exception: Follow @JetBlueCheeps on Twitter for #JetBlueFlashFares, which are one-way tickets starting at $20. These can sell out within the hour, leaving no time for third-party aggregation.

Rewards Members: Hire These Nerds

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