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Booking holiday travel? Why you and your family may see different flight prices

Experts say now is the time to start booking travel for Thanksgiving or the winter holidays.

Tara Rosenblum

and

Lee Danuff

Sep 21, 2026, 6:17 AM

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The strategies for finding the best deals have changed, thanks to dynamic pricing and artificial intelligence.

Dynamic pricing is a strategy that changes prices in real time based on supply and demand, inventory, competitor pricing, among other things.

Dynamic pricing has been around for years, but experts say artificial intelligence is making it even more sophisticated - and in some cases, more expensive.

Delta has said that they are testing AI pricing on a percentage of their flight bookings. And so it could potentially mean that if you or someone in your family is searching for the same flight at the same time, you might be shown two different prices," says Becky Blaine, managing editor of The Points Guy.

A personalized layer can also be added to the equation that could make it even harder to know if someone is truly getting the best deal.

What's new is the the AI personalization, kind of coming up with an algorithm of what you in particular might be willing to pay for a flight before you hit that pain point and decide not to purchase," says Blaine.

The good news

Blaine says there are some powerful online tools that can help level the playing field.

Google Flights, for example, can track historical pricing and alert consumers to fare drops.

Blaine says once a trip is booked, newer services like Junova and Paiback can keep watching the flights that were purchased.

If the price drops, the services can help secure a flight credit from the airline without having to constantly monitor the fare yourself - although they do charge a percentage of the savings as a fee.

The Points Guy team has been testing the services.

One writer said she got $173 back off of four different flights - in just one week.

Blaine says those thinking about traveling around Thanksgiving, Christmas or New Year's should not wait.

Experts say we're already entering the prime booking window for holiday travel - and if your schedule allows, consider traveling on the actual holiday itself.

It's often less crowded - and sometimes cheaper - than flying the days right before or after.

HELPFUL LINKS:

The tool that found me multiple surprise flight credits worth $173 this week

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