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Updated October , 2026
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Quick answer: Book Thanksgiving and Christmas 2026 flights by October 31, and fly on the holiday itself if you can. The biggest family savings come from cutting bag fees (a family of four can pay $360 round trip on Southwest alone), using the free family seating rules on United and JetBlue, and redeeming points when holiday cash fares spike. Use hotel points for the nights in between.
Flying with kids over the holidays is the travel equivalent of hosting Thanksgiving dinner in a studio apartment. It can be done. It just costs more, takes longer, and someone is going to cry.
The good news: most of the extra cost is avoidable if you move early and know the rules airlines changed this year. Southwest in particular is a different airline than it was 18 months ago, and plenty of families are about to find that out at the bag counter.
Here are the dates to plan around, then 11 ways to keep more of your money.
Key holiday travel dates for 2026
The most expensive day to fly home is usually the Sunday after Thanksgiving. If you can stay one extra day, do it.
1. When should you book Thanksgiving flights? Now.
AAA's booking data shows the holiday rush starts in late September, and most Thanksgiving flights get booked between then and late October. Every major fare-tracking source lands in the same place for 2026: book by October 31.
Set a free Google Flights price alert today for your exact route. If the fare drops after you book, Southwest, United, and JetBlue main cabin fares carry no change fee, so you can rebook and keep the difference as a credit.
2. Lock in Christmas flights by Halloween
Christmas lands on a Friday this year, and so does New Year's Day, which squeezes everyone into the same two weekends. Fare trackers agree the safe deadline is October 31.
Yes, last-minute deals sometimes show up 7 to 13 days before Christmas. With kids, you're betting on getting four seats together on a nearly full plane. That's not a bet I'd take.
3. Fly on the holiday itself
The cheapest seats are on the days nobody wants: Thanksgiving morning, Christmas Eve, Christmas Day. AAA found Christmas Eve had the lowest average fare and the lightest crowds of the week.
Bonus for parents: emptier airports mean shorter security lines and a better shot at an empty row for the toddler to sprawl across.
4. How do you avoid checked bag fees with kids?
This is where families lose the most money without noticing.
Southwest ended "bags fly free" in May 2025. For tickets booked on or after April 9, 2026, the first checked bag costs $45 and the second $55, each way. One bag per person for a family of four, there and back: 4 × $45 × 2 = $360.
The fix is a co-branded airline card. Every Southwest Rapid Rewards credit card gives a free first checked bag to the cardholder plus up to 8 people on the same reservation. Book the whole family on one reservation and that $360 goes to zero. Southwest Rapid Rewards
United and JetBlue cards offer similar first-bag perks, though the number of companions covered varies. Check before you assume the whole family is included. United Rewards JetBlue Rewards
No card? Pack one shared checked bag for the kids instead of one each, and weigh it at home. Car seats and strollers check free on most U.S. airlines.
5. Can kids sit next to you for free?
On some airlines, yes, and it's worth choosing your airline around it.
United also lets you switch for free to another flight with seats together if none are available on yours. On Southwest, book early and budget for seat selection if keeping the family together matters.
6. Earn the Southwest Companion Pass
Open seating and free bags are gone, but the Companion Pass survived. It lets one designated person fly with you for just taxes and fees, on every flight, for the rest of that year and all of the next.
For a family flying several times a year, that's one free ticket on every trip. Southwest cards also deposit 10,000 Companion Pass qualifying points each January, which gets you a head start. Earn the pass early in a calendar year to get the most use out of it.
7. Should you use points or cash for holiday flights?
Holiday cash fares are some of the highest of the year, which makes it the best time to spend points.
The trick is where you redeem. Flexible card points, like Chase Ultimate Rewards, are often worth more when transferred to a partner like United, Southwest, or Hyatt than when booked through the card's travel portal. In our credit card guide, 80,000 points were worth about $1,000 through the portal but $1,400 to $2,000 when transferred.
Two more moves: check if grandparents or siblings can pool points toward the same trip, and log into every airline and hotel account now. Points nobody remembers are points nobody uses.
8. Use hotel points for the nights in between
Not every holiday trip ends on Grandma's air mattress. For the nights on the road or near the airport:
Marriott Bonvoy: Book five award nights and the fifth is free on standard redemptions.
World of Hyatt: Award stays skip resort fees, which adds up at holiday rates. Hyatt Place and Hyatt House rooms are also roomier than most for a family.
Call the hotel after booking to ask for connecting rooms or a crib. It costs nothing to ask.
9. Check every airport within driving distance
If you live in a metro area with two or three airports, compare all of them. A secondary airport can save a few hundred dollars for a family, plus shorter security lines. Do the full math, though: parking, gas, and an extra hour in the car with kids all count.
10. Drive if the math says so
For a family of four, flying multiplies every cost by four: fares, bags, airport food. A drive of six or seven hours often costs less than one round-trip ticket. Leave early on the travel day or the night before, when roads are lightest.
11. Dodge the airport upsells
The airport is designed to separate parents from money. Pack snacks, bring empty water bottles to fill after security, and download shows before you leave the house so you're not buying in-flight Wi-Fi to save your sanity.
The bottom line
Holiday travel with kids doesn't have to wreck your December budget. Book by Halloween, fly on the holiday itself, and stop paying bag fees you don't have to pay. Then let points cover the rest.
Want more ways to stretch your family's money? Every Wednesday, Knocked-Up Money sends parents and parents-to-be practical money moves: side hustles, smart savings, investing basics, and travel deals like these.
Need extra cash for the trip? Here's how much you can make donating plasma and our 12 best side hustles for families.
FAQ: Holiday travel with kids in 2026
When should I book Thanksgiving flights for 2026? Book by October 31, 2026. Thanksgiving is Thursday, November 26. The cheapest days to fly are usually Thanksgiving Day itself and the Monday of Thanksgiving week.
When should I book Christmas flights for 2026? Aim to book by Halloween. Christmas 2026 falls on a Friday, and Christmas Eve and Christmas Day are typically the cheapest days to fly.
Does Southwest still give free checked bags? Not on most fares. For tickets booked on or after April 9, 2026, the first bag is $45 and the second $55 each way. Southwest credit cardholders get a free first bag for themselves and up to 8 people on the same reservation.
Can my kids sit next to me for free? On United, children under 12 can sit next to an adult for free, even in Basic Economy. On JetBlue, kids 13 and under can sit next to an adult on the same reservation on any fare. Southwest switched to assigned seating in January 2026 and does not guarantee free adjacent seats, so book early.
Is it better to pay cash or use points for holiday flights? Holiday cash fares are high, which often makes points the better deal. Transferring flexible points to an airline or hotel partner usually gets more value than redeeming through a card's travel portal.
