The Best Time to Book Holiday Flights (And the Dates That Will Save You the Most)

Every year, right around the time the pumpkins show up on porches, the same question starts popping up in every moms group I'm in: "When should I book flights for Christmas?" Usually it's followed by a screenshot of a fare that looks more like a mortgage payment, and fifty comments of people saying "Tuesday!" or "Wait until the last minute!" or "Use incognito mode!" (I love you all, but no.)

Holiday airfare is one of those things where a little timing makes a huge difference. So here's what I tell my own family and friends when they ask me for insider info.

Airport play area for kids at MKE

Book Before Halloween (Mid-October Is the Sweet Spot)

If you're flying in late December, the best time to book is before Halloween, and ideally right around mid-October. I know it feels early when you haven't even figured out what your kids are going to be for trick-or-treat, but this is the window where airlines still have plenty of seats at their lower fare levels and haven't started squeezing holiday travelers yet.

Once November hits, those cheaper fare buckets start selling out, and prices tend to climb steadily from there. The "wait for a last-minute deal" strategy works for a random weekend in February, but it almost never works the week of Christmas, because the planes are going to be full whether or not the airline drops the price.

So if you've been telling yourself you'll look at flights "after Halloween," I'd gently suggest you look this week instead.

Fly Out Between December 18 and 22

If you have any flexibility at all, leaving between Friday, December 18 and Tuesday, December 22 will usually get you better prices than waiting until the 23rd or Christmas Eve. Those last couple of days before Christmas are when everyone who "couldn't get away earlier" piles onto the same flights, and the fares reflect that.

The nice part is that this window tends to line up pretty well with real life. A lot of schools let out for winter break right around the 18th or 19th, and plenty of offices slow way down that week anyway. If you can take a day or two of PTO to leave on a Saturday, Monday, or Tuesday instead of the 23rd, you'll usually save money and skip some of the worst airport crowds (which, if you've ever navigated a security line with a toddler and a stroller on December 23, is worth a lot on its own).

Whatever You Do, Avoid Coming Home on Sunday, December 27

This year, December 27 falls on a Sunday, and it's shaping up to be one of the most expensive days to fly home. Think about who's on that flight: every family that flew out for Christmas and needs to be back for work on Monday, plus every college student heading back early, plus everyone who just wants a day to unpack before real life starts again.

If you can come home a day or two earlier, or stretch the trip a little later, you'll usually see a noticeable price difference. Plug a few different return dates into your search and compare, because your future self who doesn't have to sprint through a packed terminal will thank you.

Easy Jet flight over Australia

The Best Deal Nobody Thinks About: December 31

Here's the thing nobody tells you about holiday travel: New Year's Eve is typically one of the cheapest days of the whole season to fly. Most people want to be settled somewhere with a glass of champagne by then, not sitting at gate B14, so demand drops and fares usually follow.

If your family is fine with a low-key New Year's (and let's be honest, if you have little kids, you're probably celebrating at 9 p.m. anyway), flying home on the 31st can save you a surprising amount. It also gives you a full extra week of holiday visiting, which is either a bonus or a warning depending on your relatives.

Your Holiday Flight Cheat Sheet

Book your flights: Before Halloween, ideally mid-October. Lower fares are still available before the November price climb.

Fly out: Friday, Dec. 18 to Tuesday, Dec. 22. It's cheaper than the 23rd and 24th, and it lines up with most school breaks.

Avoid returning: Sunday, Dec. 27. Everyone is flying home before work on Monday.

Best deal of the season: Thursday, Dec. 31. Demand drops because most people are already where they want to be.I'll be honest with you: holiday travel is never going to be cheap, and there's no magic button that makes a flight home for Christmas cost the same as a random Tuesday in March. But booking in mid-October, leaving a few days early, skipping that Sunday return, and keeping December 31 in your back pocket can make a noticeable difference in what you pay, and every dollar you save is a little more room in the Santa budget.

If you're staring at a dozen browser tabs and would rather hand this off to someone who does it every day, I'd love to help.