Why You Should Always Book Travel During the Opposite Season

Many travelers don’t start thinking about summer flights until the summer, or winter flights until the winter. (Understandably!)

The problem is that summer is the most expensive time of year to book summer flights, and November/December is the toughest time to find a good winter holiday flight.

If you’ve got a cheap-flight-loving heart, the best strategy is, instead, to book during the opposite season.‍

Always book opposite season

‍It’s usually around May that I start getting asked how to find cheap summer flights. I do all I can to help—I’m not a jerk!—but I generally have to bite my tongue on what I really want to say: you should have asked months ago.

If you only start thinking about summer flights once summer is almost here, your odds of getting a cheap flight are not great.

Instead, the best approach to getting cheap peak season flights is simple. Book opposite season.

Much like how swimsuits are cheaper in the winter and coats are cheaper in the summer, so too are summer flights generally cheaper when you book them in the winter.

So when you’re at your July 4th BBQ, that’s when you should start looking about winter holiday flights. And when you’re getting dolled up for that New Year’s ball, that’s when you should start looking about summer flights.

>> Read our guide to finding cheap summer flights or our guide to snagging great deals for Christmas trips.

The reason why booking opposite season is a good strategy if you’re traveling in peak season? Because it falls within the Goldilocks Windows.‍

Further-out bookings produce the most joy

‍One of the most interesting things I learned while researching Take More Vacations was the way travel actually brings us joy.

We think of vacation as something we only enjoy during the trip itself.

But if you dig into the research, it turns out we get as much if not more joy before a trip, daydreaming about sipping cocktails on the beach or perusing weekend markets. Anticipation is a hell of a drug.

When does a trip become real in our minds? Not when we first imagine it or even when we start researching it. A trip becomes real the moment we book flights—that’s when it starts bringing us joy.

While few people today are thinking about travel next summer, I think that’s exactly what you should do if you want cheap flights and more happiness. Treat your future self and your today self by having a trip to look forward to.

Goldilocks Windows

‍While there’s no cheapest day or time to book flights—“Tuesday at 1 pm” is a myth—there are periods in advance of travel when cheap flights are most likely to pop up. I call these Goldilocks Windows.

If you’re traveling domestically, the Goldilocks Window for when you’re most likely to see a cheap flight is 1-3 months before flying. For international flights, it’s 2-8 months in advance.

But if you’re hoping to travel during a peak time like middle of summer or around New Year’s, you’ll need to add a few months. More like 3-6 months for domestic flights and 3-10 months for international.

Things may be a bit different this year

‍In normal times, “cheap last-minute flights” is an oxymoron. But as with many aspects of society, the pandemic has temporarily complicated airfare.

We’re seeing far more cheap last-minute flights than we would in typical years. But the last few years have been anything but year.

Here's why

1. Lingering hesitancy about international travel. Even as travel rebounds, the number of Americans traveling internationally is still down. As a result, international flights have far more unsold seats than they did in 2019, and airlines are slashing fares to fill them.
2. Airlines focus on business class revenue. Decades ago, airlines made most of their money on economy airfares. Nowadays, they make most of their money on revenue sources other than economy fares, things like selling frequent flyer miles, credit cards, corporate contracts, cargo, and yes, expensive business class seats. Long-haul international flights are often quite pricey in business class—normally $2,500+ roundtrip to Europe—which is one reason we launched our Elite service to flag great front-of-the-plane deals. But those pricey business class fares, in effect, subsidize economy flyers and allow airlines to offer <$400 Europe flights.
3. Vacationers are price sensitive. If flights to Greece cost $1,200, vacationers will just go to Spain, or Nashville, or take a roadtrip instead. What’s the easiest way for airlines to entice price-sensitive leisure travelers? Cheap flights.

But the perfect storm that’s enabling currently cheap last-minute flights is unlikely to persist very far into 2022. So if you’re hoping for a cheap summer 2022 flight, the advice still stands: book opposite season.

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