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By The Way
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This cheap flights expert thinks you should be booking trips earlier

Better travel comes from trips planned further in advance, according to Going founder Scott Keyes

(Illustration by Min Heo for The Washington Post)

Welcome to The Upgrade, By The Way’s series on travel hacks and hot takes. See how to submit here.

A classic travel trope you’ve probably heard at a bar or party is the notion of simply showing up at the airport, picking a destination from the flight board and going.

Under the harsh lights of sobriety, the idea is patently ridiculous, of course. How would you pack? But what I’m here to argue isn’t that last-minute travel is flawed logistically; rather, it’s flawed qualitatively.

If you have a choice, better travel comes from trips planned further in advance.

There are three primary reasons to plan further in advance: cheaper flights; taking advantage of newfound flexibility; and extended happiness.

First, advanced planning means cheaper flights. It’s well understood by now that last-minute airfare gets hideously expensive. But if you’re hoping for truly great deals — such as those recent $316 round-trip flights to Tokyo — booking a few weeks out isn’t enough. Many of the best deals are found three to nine months out.

How do you actually get those $49 flights? There’s always a catch to airline sales.

The best way to time your bookings isn’t by buying flights on a Tuesday at 1 p.m. (advice that worked decades ago but no longer helps) or exactly 63 days before travel. Instead, it’s by booking during a “Goldilocks Window,” the period ahead of travel when cheap flights are most likely to pop up. For domestic travel, that’s one to three months out, and for international flights, it’s more like two to eight months. For peak season, when deals are harder to come by, add a few months to those recommendations. Not every flight is cheap during a Goldilocks Window, but it’s when your odds of a fare drop are at their best. (And, of course, you only need the fare to drop once.)

Plus, if the primary constraint on your travels is money, as opposed to time, then cheaper flights mean more trips.

Second, planning travel further in advance is less risky now that airlines allow free changes. The common objection of “What if my plans change?” is understandable. Fortunately, it’s less palpable now. Pre-pandemic, it would often cost $200 — plus any fare difference — just to switch your travel dates. But in late 2020, airlines announced they were permanently scrapping change fees. Today, you can switch your travel dates (and only cover any fare difference, or get a credit if the new flight is cheaper) or cancel altogether and get travel credit for the full amount of the ticket without having to sacrifice hundreds of dollars in fees. Note: Free changes aren’t permitted on basic economy tickets or on budget airlines like Spirit.

With free changes, if you decide not to take that Japan trip you booked, you can switch your dates or even your destination without a penalty. In other words, you can make your travel plans in pencil rather than in pen.

Third, and perhaps most importantly, trips planned further out give you more joy. One of the more common mistakes is thinking of travel as something we only enjoy during a trip itself. Just grit your teeth until the summer, when you’ll finally get to enjoy yourself at that Parisian sidewalk cafe or on that beach lounger in Miami.

But in fact, study after study finds that we get as much, if not more, joy from anticipating a vacation than actually being on vacation itself. This may be surprising, but consider: In our daydreams about a vacation, we’re never sweaty or hangry or disappointed the way we sometimes are when we’re on a trip.

What’s more, planning further out doesn’t detract from the happiness you’ll feel during the trip. There’s not a fixed amount of joy you’ll get from a trip; starting earlier extends the benefits of travel.

In other words, our future selves aren’t the only ones who enjoy Paris or Miami; our current selves do, too. And what is the seminal moment when a travel dream becomes a travel reality that begins really paying happiness dividends? The moment you book your flight.

Scott Keyes is the founder of, a cheap flight alert service with more than 2 million members. When he’s not on a plane, Keyes lives with his family in Portland, Ore.