How to Get Ahead of Travel Nightmares This Holiday Season

Hopefully you’ve heeded the experts and booked your end-of-year travel earlier than you did last year. But no matter how well you’ve gotten ahead of your holiday plans, if you’re one of the almost 50% of Americans who say they’re traveling sometime between Thanksgiving weekend and January, there’s a good chance you could experience disruptions this winter season.

Almost a quarter (24%) of flights out of US airports have faced delays so far this year, according to the US Department of Transportation—up from 19% in 2021. That means your flight has a more than 1 in 5 chance of not leaving on time. The winter storms and technology issues that snarled operations for Southwest Airlines Co. in December 2022 could easily affect a different carrier this season, says Mike Arnot, an airline industry analyst and spokesperson for aviation data company Cirium.

Yet, US airlines are better prepared for operational challenges this season, experts at Cirium and travel-booking platform Hopper say. “Last holiday season, airlines were trying to run a lot of capacity to capture holiday demand, but they were stretched thin as it was challenging to get staffing,” says Hayley Berg, lead economist at Hopper, adding that those worker shortages have since been alleviated. Still, your best bet is to stay on your toes and use all the latest tools to confront potential disruptions.

Prebook Airport Rides

Consider that ride-sharing companies are likely to face peak demand during the holiday period. With bigger crowds on the road, travel time to reach the airport can also increase. 

Earlier this year, Uber Technologies Inc. opened up ride reservations for up to 90 days in advance, a bump from the usual 30-day window that’s available on Lyft. This ensures a driver will be assigned to get you to the airport on time, rather than leaving it to chance, and you get to lock in the indicated fare.

Lyft is taking it one step further this holiday season. Starting on Nov. 9 you can expect an “on-time pickup promise” for reserved rides in most major markets. This guarantees the driver will arrive within 10 minutes of your chosen pickup time. If the driver fails to show up inside those 10 minutes, you’ll receive a $20 Lyft credit. That goes up to $50 if you’re not matched with a driver within 10 minutes after your scheduled pickup time. If you have to resort to using another service—say, a taxi or an Uber—Lyft says it will credit the user another $50, for a maximum payout of $100.

Know the Most Affected Airports

Hopper is predicting that the following 10 US airports will have the greatest share of winter travel disruptions this year. The list is based on flight delay and cancellation data from the past three months, as well as the last two weeks of December 2022: basically an airport’s performance last holiday season plus its more recent track record. Here are the expected losers, in descending order. 

10. Dallas Love Field (DAL)

9. Dallas Fort-Worth (DFW)

8. Baltimore (BWI)

7. Fort Lauderdale (FLL)

6. New York City (JFK)

5. Newark, New Jersey (EWR)

4. Chicago Midway (MDW)

3. Las Vegas (LAS)

2. Orlando (MCO)

1. Denver (DEN)

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Avoid the Most Hectic Travel Days

Sunday, Nov. 26, will be the busiest travel day of the year in the US, according to Cirium, based on the number of passengers flying (almost 3.1 million) and flights scheduled (more than 22,00). Other days that Cirium sees as being especially busy during the holiday season: Dec. 21, 22, 28 and 29, and Jan. 2 and 7. 

Aside from showing up earlier than required and bringing a solid dose of patience, you could build in a buffer day, so any special events or celebratory days aren’t missed.

If you’re driving to see family for Thanksgiving, know that peak traffic days that week are Tuesday and Wednesday, around 4 p.m. to 5 p.m., according to Google Maps data that examined traffic patterns in more than 20 major cities across the US during the same period last year. Your best bet, the company says, is to hit the road on Monday or Tuesday at 8 p.m. local time. 

Have a Contingency Plan

If a flight delay strikes and you’re a relatively short distance from your final stop, plan for alternate ways to get there. Berlin-based premium-car-service company Blacklane, for example, kicked off US city-to-city chauffeured routes in May 2023. Rates start at $150 one-way, with a newly expanded route network that includes New York to Baltimore, Los Angeles to San Diego, Denver to Aspen and Dallas to Austin. Expect to cruise in a Cadillac Escalade, or a Mercedes-Benz E-Class or S-Class, among other similar luxury models. 

“We are increasing the distances that we serve in more and more cities, replacing things like short-haul flights, which are super uncomfortable, super unsustainable, full of stress and delays,” says Jens Wohltorf, chief executive officer and founder of Blacklane. You can prebook your city-to-city ride on the company’s app or online, down to an hour before pickup. 

If you should get stranded overnight with thousands of other travelers, resist the impulse to book at the nearest airport hotel, which tend to fill up quickly and may jack up prices when a massive storm sends swells of passengers into crisis mode all at once. A more pleasant solution is to book a hotel in the city—apps such as Hopper, Kayak or HotelTonight will highlight deals that most other stranded flyers won’t be snapping up. You’ll also save yourself the grief of standing in long check-in lines at the airport hotel.

Finally, remember to purchase adequate travel insurance coverage. So far this year about 25% of all travel insurance claims have been for delays, says Steven Benna, marketing manager at Florida-based comparison-shopping site Squaremouth, which is consistent with 2022. If you’re delayed at least three hours, most policy holders can expect to see an average payout of more than $485 for out-of-pocket expenses, with additional coverage for missed connections.

Procrastination won’t pay off here: If a winter storm is announced a week before your journey begins and you’ve waited to purchase insurance, you can expect to be refused coverage when that storm disrupts your journey.