Winter holiday travel: Pounce now on flights or roll the dice?

By Forrest Brown, CNN

The high prices, the canceled flights, the booked-up lodging and rental cars. The summer of travel chaos still seems hot and fresh somehow.

But it’s time to look forward, for there’s another crunch time looming less than two months away: the 2022 winter holiday travel season.

So put away your T-shirts, break out your sweaters and get ready for the winter holidays. Here’s what to know:

When should I buy tickets for winter holiday flights?

Decision-making on when to buy airline tickets seems more complicated that ever. Prices change daily, even hourly. The staffing and capacity ramifications of the pandemic are still being felt.

But October is probably the best window of opportunity. In other words, NOW.

“Typically … travelers tend to start planning their holiday travel too late, and they miss out on some of the best prices available,” said Hayley Berg, lead economist at Hopper, the planning and booking travel app. And she told CNN Travel she is seeing people waiting later than ever to seal the deal during the pandemic rebound.

“For the holidays in particular, that’s a real problem because now is actually the best time to be booking your Thanksgiving and Christmas travel,” Berg said.

Hopper suggested in an email to wait no later than mid-October.

It’s not just a pricing issue, Berg said. She also noted another risk by waiting: “Flights may be sold out completely on the dates you want to fly.”

The worst time to book? ‘The last minute’

Scott Keyes, the founder of flight deals and travel advice site Scott’s Cheap Flights, told CNN Travel the very best deals were actually this past summer (remember that for 2023). But don’t be discouraged this year, he said.

“The second best time to be booking your flights is now — because the worst time to book them is to wait until the last minute,” Keyes said. “If you haven’t booked those flights already and you’re really hoping to travel over the winter holidays, try to get it booked in the next week or two.”

Keyes thinks air fares are likely to get more expensive, not less, as we get closer to Thanksgiving and Christmas.

Phil Dengler, a co-owner of the travel resource The Vacationer, uses a popular fall holiday as his guide.

“I view Halloween as the cutoff date for getting a reasonable price on a Thanksgiving flight, but aim to get booked before then,” Dengler said in an email interview. “After Halloween, prices will increase considerably as Thanksgiving gets closer. For Christmas flights, you should really book before Thanksgiving, but the best deals are between now and Halloween.”

The auto and travel club AAA had different pricing data for Thanksgiving air fares.

Based on booking data from 2019, 2021 and 2022 so far, AAA found the lowest average fares just seven to 14 days before Thanksgiving, with the highest prices 28 to 60 days before the holiday. However, the data also showed prices rising in the last seven days before the holiday.

So should you wait? A lot depends on personal circumstances such as your budget and how flexible you are with your flying plans, AAA told CNN Travel. If you don’t have a lot of wiggle room, it might not be worth the risk to wait for a chance at a lower fare.

“Airlines have fewer flights than they did in 2019, which means fewer options for consumers,” said AAA’s Paula Twidale, senior vice president of travel. “With staff shortages and capacity being at its peak, you run the risk of being delayed or even missing flights, particularly if weather plays into the equation.”

What are the best days to fly for Thanksgiving?

Expedia shared some insights on when to travel for Thanksgiving (Thursday, November 24):

To save money, the travel company suggested waiting until Monday (November 21) to depart instead of Saturday (November 19) and Sunday (November 20), “as the weekend is the most expensive time to start your Thanksgiving week trip.”

Average ticket prices for Monday are more than 30% lower than Saturday and nearly 15% cheaper than Wednesday (November 23), it said.

As for returns, Expedia said Friday (November 25) is the cheapest date. Coming back Monday (November 28) instead of Sunday (November 27) could save from 5% to 10%.

Hopper also suggests flying Thanksgiving Day if you can, offering savings of around $100 off peak prices. Plus planes should be less crowded.

Keyes said the Thanksgiving weekend comes with a bonus. “Thanksgiving is the hidden best week for international travel,” Keyes said.

Why is that?

Christmas and New Year’s are celebrated worldwide and thus come with global demand, but Thanksgiving is just a US holiday, he said. Domestic flights are pricey, but not international ones.

“You find some incredible deals all throughout Europe over Thanksgiving week.” He said that on one price check this week, he found cheaper fare from New York City to Lisbon, Portugal ($429 round-trip, than to Cedar Rapids, Iowa ($567 round-trip).

What are the best days to fly for Christmas?

Hopper had advice on when to travel for Christmas (Sunday, December 25):

For departure, it said travelers can save $120 off peak prices by departing the Monday (December 19) or Tuesday (December 20) before Christmas. Leaving on Christmas Eve could save people about $100 this year, Hopper estimated. The site said avoid flying out Thursday (December 22) or Friday (December 23), as those will be the most expensive travel days.

For returns, the Tuesday (December 27) or Wednesday (December 28) after Christmas Day could save you $40 per ticket. It said avoid coming back on Monday (December 26), New Year’s Day or January 2, the most expensive return dates.

Some other tips from the experts

Have your ducks in a row: “Preparation is the best way to reduce stress when flying over Thanksgiving and Christmas,” Dengler said. “If possible, book a nonstop flight early in the morning” on a lower-volume travel day. He also advised not checking a bag if possible.

Treat yourself: If you fly several times a year or more and value a low stress level, Keyes suggested getting a credit card that includes “compelling perks.” That includes access to special airport lounges that get you away from the crowds and offer free food, drinks and even massages.

Avoid the rush: If you’re driving, Twidale said leave early in the morning before rush hour or after 8 p.m. If you need a rental car, reserve it early to lock into the rate and pay in advance to save money. If you’re flying but driving to the airport, book parking spaces. She also suggested enrolling in TSA Pre-check to bypass long security lines.

Hotels: Berg said if you’re headed to a big city (think New York, Chicago, etc.), you are likely to get a better deal if you wait until just a few days before your arrival date to book the room. The caveats: This is for people who aren’t dead set on a certain hotel or specific neighborhood. And for smaller cities, she said people should still book earlier as choices are limited.

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Top image: The United Airlines ticket counter at Reagan National Airport in Arlington, Virginia on Christmas Eve 2021. (Eric Lee/Bloomberg via Getty Images)