How To Find Cheap Flights Even if You Can’t Be Flexible With Time or Place

There are two big buckets of trips: those where you have lots of flexibility and those where you have little flexibility. You never want to overpay for flights, but the strategy to get a good deal varies significantly based on which type of trip you’re taking.

We often talk about how you should reverse your search to get the best deals when you have a good amount of flexibility. But when you’ve got to be somewhere at a specific time—your sister’s wedding in Chicago next June, say—the best thing you can do to avoid overpaying is to time your booking right.

Goldilocks Window

There’s no set time or date that’s always cheapest to book. (Internet myths like Tuesday at 1pm or exactly 63 days out are dead wrong.)

Instead, the best approach is to target a period in advance of travel when cheap fares are most likely to pop up. I call these Goldilocks Windows.

For domestic flights, it’s normally 1–3 months before your travel dates. For international trips, it’s 2–8 months prior. If your trip is during a peak travel period (Christmas, summer, St. Patrick’s Day in Dublin) add a couple months to those windows.

Not every flight is cheap during a Goldilocks Window, just as not every day is snowy in winter. But it’s the period when your odds of a good deal are at their highest.

Fly nearby

We’ve talked about the Greek Islands Trick to get cheaper flights. If fares are staying persistently high for a trip you’re eyeing, this can be useful.

Say you want to visit NYC for New Year’s, but flights are $700 or more. Instead of accepting an outrageous price, see what flights to Philadelphia, Hartford, Boston, or DC cost. If you find a deal to Philadelphia for $200, the question then becomes: Would you be willing to take the train from Philadelphia to NYC in order to save $500?

The same can apply for your departure flight. A Going member Shanna Lathwell once wanted to take her family of five from Detroit to Bali for spring break, but flight prices were $2,500 each. One day, she got an alert from Going about flights from Chicago to Bali for just $500 each. Was the four-hour drive from Detroit to Chicago worth it to save $10,000 total on flights? No question.

Book now, rebook later

How often have you had the anxiety that prices will drop right after you book a flight? If so, you’re in luck.

One of the most customer-friendly shifts in the past few years has been airlines getting rid of change fees. Pre-pandemic, there was often a $100+ penalty to change your flights, in addition to any fare difference. Starting in late 2020, though, US airlines got rid of change fees en masse. (Basic economy tickets are still restricted, unfortunately.)

This has given travelers a heads-you-win, tails-airlines-lose opportunity: If the price of your flight drops after booking, you can rebook and pocket the difference in future travel credit.

Take a recent $400 flight I booked to Denver, for instance. After booking, I set myself a calendar reminder to check the price every Monday morning. Sure enough, three weeks later, the price had dropped to $300. I called Alaska Airlines, asked the agent to rebook it, and five minutes later had the same flight plus $100 in travel credit.

If the price keeps dropping, you can keep rebooking. That Denver flight wound up dropping two more times—all the way down to $175—and each time I rebooked for additional credit.

The bottom line

Flexibility is a currency, and for trips where there’s little flexibility, that often means higher fares. But just because you can’t get the best prices doesn’t mean you should give in and overpay. By getting the timing of your booking right and employing a few tricks, even trips with little flexibility can still see great prices.