There’s so much to look forward to in the winter, from seeing family on the holidays to celebrating a new year with friends to finding the perfect gift for your favorite person. And now you want to take a winter trip, escape the cold of home, or break out of a rut and experience something extraordinary.
Winter travel can present some challenges, whether it’s snowstorms that cause flight delays or bad road conditions, seasonal illness, or just the high stress of the season. But traveling in winter also offers opportunities you won’t find at other times of the year. Cold-weather sports, seasonal festivals, breathtaking winter scenery, and holiday decorations in the streets can all make it worth the extra effort.
Everything you need to make the most of your holiday vacation — and to make it easy and stress-free — is right here.
When Is the Best Time to Book Holiday Travel?
The general rule for holiday travel booking is to do it sooner rather than later. Ideally, you’ve made all your bookings by October. Yes, you could wait until the last minute to try to snag a great deal, but it’s also possible you’ll end up getting nothing instead.
Popular destinations will fill up quickly, making it difficult if not impossible, to find a hotel reservation, a vacation home in the location you want (or with the number of bedrooms you need), a table at the restaurant you’ve been dreaming of, or tickets to the show you planned on treating your family to.
If you’re not picky and are more concerned about scoring a good deal than getting a suite at the perfect hotel, you could wait until about a week before your trip. Just be prepared to adjust your plans and expectations.
When Is the Best Time to Book a Flight for the Holidays?
When it comes to flying at the holidays, aim for buying your plane tickets by the end of October. Much later than that and you’ll find that flight prices increase the closer you get to Thanksgiving. If you look at the first chart below, you'll see that the airfare for a one-way flight from Indianapolis to Portland, Oregon, the Saturday before Thanksgiving cost about $285 when I checked prices on Oct. 1. However, when I ran the test about six weeks earlier, in mid-August, the airfare was just $165.
You can also see in the chart below how the cost of airfare for Thanksgiving travel changes depending on when you fly. It might be worth adjusting your schedule a day or two if you need to save money.
Cost of Southwest Airlines Airfare, Indianapolis to Portland, Oregon, Prior to Thanksgiving 2025
| Date | Airfare |
|---|---|
| Saturday, Nov. 22 | $285 |
| Sunday, Nov. 23 | $339 |
| Monday, Nov. 24 | $309 |
| Tuesday, Nov. 25 | $309 |
| Wednesday, Nov. 26 | $339 |
| Thanksgiving Day | $238 |
| *Research conducted October 1, 2025 | |
We see similar price fluctuations for the week leading up to Christmas. The most jarring shift came when I compared prices from mid-August to what I found in early October. For a flight on Dec. 23, there was a $243 increase from the first time I checked prices to the next.
Cost of Southwest Airlines Airfare, Indianapolis to Portland, Oregon, Prior to Christmas 2025
| Date | Airfare |
|---|---|
| Thursday, Dec. 18 | $274 |
| Friday, Dec. 19 | $309 |
| Saturday, Dec. 20 | $426 |
| Sunday, Dec. 21 | $309 |
| Monday, Dec. 22 | $339 |
| Tuesday, Dec. 23 | $421 |
| Wednesday, Dec. 24 | $304 |
| Thursday, Dec. 25 | $344 |
| *Research conducted October 1, 2025 | |
It’s incredibly rare for prices to dip in December, even as you get closer to the end of the month. During more typical travel times, we recommend buying tickets about a month before a domestic flight and three to four months before an international one. With the holidays or other peak seasons, though, extend that timeline even more.
What Are the Busiest Holiday Travel Days?
At Thanksgiving, the busiest travel days are historically the Wednesday before and the Sunday after the holiday. There was a short-lived exception the year or two when travel re-opened after the COVID pandemic, but trends seem to have rebounded back to normal.
TSA screened a record 3.08 million passengers on the Sunday after Thanksgiving in 2024. That was up from 2.56 million in 2022 and 2.9 million in 2023. This year, we wouldn’t be surprised to see this trend continue. Expect the busiest travels days to again be the Tuesday and Wednesday before Thanksgiving and the Sunday after the holiday.
Let’s look at December. Before the pandemic, some reports found December 17 was the busiest travel day, meaning travelers were starting their vacations one week before Christmas. Christmas Eve was the second busiest day.
For those with the flexibility to work remotely, that trend could very well continue. Those who aren’t able to be away for quite so long will likely still opt to fly the weekend before Christmas, on December 20 or 21, in 2025.
With Christmas in 2025 falling on a Thursday, the weekend after the holiday will be busy as well as people return home. If you want to avoid the crowds and chaos, see if you can squeeze out one more day of vacation and fly home on Monday, Dec. 29.
To get around the hassle of busy airports and roads, try to be flexible with your own travel dates. Maybe that means leaving a day or two earlier, and maybe it means you fly on the holiday. We know it’s less convenient, but that’s why it tends to be cheaper and less hectic.
Winter Vacation Travel Tips
A few travel hacks worked out ahead of time can be the difference between a happy holiday and a woeful winter.
1. Start planning early.
By planning your trip early, you’re more likely to find great travel deals. You can set price alerts for flights and monitor how the cost of airfare fluctuates before deciding the best time to buy. You can also keep an eye out for sales and spread out your spending, much like you would when shopping for gifts.
Some people might thrive under pressure, but why put yourself through that stress? Begin planning early and you’ll have time to do it at your pace, when you have time think, and it might actually be more fun.
2. Choose non-stop flights.
Flight cancellations and delays are a worry any time of year, but with the added complications of bad weather and overbooked flights, the headaches just get bigger. When you book a non-stop flight, you don’t have to worry about missing connections or your luggage not making it on the next flight.
3. Fly with carry-on only.
If you don’t check any luggage, then it can’t get lost. Plus, there’s no standing around at the baggage carousel waiting. When you want to get out of the airport and on with the festivities quickly, traveling light only with carry-on luggage is the way to go.
4. Get TSA PreCheck.
Perhaps no area in the airport is more chaotic during the holidays than security checkpoints (maybe the Starbucks line). Now might be the perfect time to finally get that TSA PreCheck, making it easier and quicker to get to your gate, even with increased holiday air traffic.
5. Treat yourself to airport lounge access.
A quiet, luxurious airport lounge might become your favorite place when you’re faced with a chaotic terminal during the holidays. Buy a day pass, upgrade your plane ticket, or check to see if your credit card offers lounge perks. Then simply sit back and relax while you unwind before departure or wait out a delay.
6. Give yourself extra time.
Build in extra time to get from Point A to Point B and avoid overscheduling with every activity you can think of. The extra time you gift yourself will reduce the chances of one small misstep dominoing into a massive problem.
Sure, holiday traffic, whether it’s at the airport or on the roads, bad weather, and over-sugared cranky kids who refuse to put on their shoes is the opposite of fun. You'll thank yourself for the wiggle room you build into your itinerary, though. After all, there’s nothing wrong with doing less on your holiday break, especially when it helps you restore your sanity and joy in the season.
7. Double-check when things are open and make reservations.
Attractions and restaurants often change their hours during holidays. Or they might close for a private party. Before loading the entire family in the car with promises of an epic holiday adventure, make sure your destination will be open.
Double-check whether reservations or advance tickets are needed. A place might not usually require reservations, but the rules could change if they’re busier than usual.
8. Start a tradition with a special travel gift.
Among her tips for making your holiday road trip easier, former Seven Corners writer Ashley Fritz recommended creating a “road trip only” tradition of picking a special gift for the kids.
For Ashley and her sisters, it was the so-called Bug Juice their dad bought them at gas stations. For your kids, maybe it’s a new coloring book or game app for their phone. Or maybe you and your loved one treat yourselves to a pre-flight mimosa.
9. Be a smart gift-giver.
We love to shower our loved ones with gifts as much as the next person, but traveling with presents can be tricky. These bonus tips will help make sure the gifts arrive on time, in one piece, and without you losing your mind.
- Pack gifts in your carry-on, if possible, so they don't get lost or delayed in checked luggage. Just make sure the gifts meet TSA rules for carry-on luggage.
- Don’t wrap gifts if you're flying with them. TSA will likely unwrap them regardless of whether they’re checked or in your carry-on. Either plan to wrap presents at your destination or use gift bags instead.
- Ship gifts ahead of time so you don’t have to pack an extra suitcase or carry them through the terminal. And if your luggage gets lost or damaged, you won’t stress about whether that perfect present you finally found for Great-Aunt Edna made it in one piece.
- Focus on experience gifts and things that don’t take up luggage space. Maybe the trip itself is the gift. Or you treat the family that’s hosting you for the holidays to a special outing while you’re there. Now’s your chance to get creative.
10. Have a plan for dealing with stress.
Sometimes we experience travel anxiety because there are so many things out of our control. If it helps, take time to plan how you’ll handle unexpected events.
Will you adjust your travel dates if the weather gets too bad? How about talking to your doctor about ways to stay healthy during holiday travel? Maybe it’s planning “me time” activities if the idea of all that quality time has you feeling on edge.
Plan for the Unexpected with Holiday Travel Insurance.
Mishaps can happen any time of year, but their frequency can increase during peak travel season. Adding to that travel stress can be the pressure to make perfect holiday memories. And then there’s the cost of it all, including trip expenses and the price of other festive activities.
Travel insurance can help protect the money you spent for your trip if you have to cancel your holiday travels, if your luggage is lost or damaged, and more. Get a quick quote online or talk to one of our licensed agents to get the best coverage for your winter holiday travel.
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