Why You Should Always Book Travel During the Opposite Season

Many travelers don’t start thinking about summer flights until summer hits. Those same travelers probably also don’t start thinking about winter flights until winter. Understandable. Time moves fast, and people are busy. But waiting too long could cost you. 

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.

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

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

Use the Goldilocks Window

‍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 the 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 the middle of summer or around New Year, you’ll need to add a few months. More like 3–6 months for domestic flights and 3–10 months for international. 

The frequency of deals during the Christmas and New Year holidays will start to dry up by the time we hit Labor Day, and if you wait until Halloween or even Thanksgiving to start looking for holiday flights, you’re likely going to pay a lot more than you should. 

What recent history tells us

As the rise in summer 2022, 2023, and 2024 fares has shown us, airlines are working double time to squeeze all the revenue they can from surges in demand. As of now, fares aren’t surging for the winter holidays yet because the demand isn't there, but as soon as the leaves start to turn and folks start scouting out their Thanksgiving and Christmas options, you can bet the house that airlines will start cranking up those fares aggressively, especially for the most popular routes.

However, early planners should also be aware that while locking in a great fare now is a good idea, once you’ve booked it, you should keep your eye on it. Airline schedules can change constantly, so booking early means you’re pretty likely to see something change with your flight—whether that means a little change in departure time or something more dramatic.

Either way, it’s important to check your flight status frequently in the months and weeks leading up to your trip and know your rights if something goes sideways (it’s not always bad, though; sometimes a schedule change can work in your favor!).

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.