Kayak’s Holiday Travel Tool Sounds Genius — But Does It Work?

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Fall is in the air and with that comes people preparing for the holiday travel season. While there’s still time to secure a cheap flight leading up to Thanksgiving, the winter holidays are right around the corner after this corner — posing a whole new set of potential travel woes. December is notorious for being the most expensive month of the year to travel, so your holiday plans may include dropping double or triple the dollars to make it home for Christmas Eve.

Knowing that the holidays pose extra stress on travelers, travel companies have started utilizing AI technology to help prospective travelers orchestrate the perfect trip. Earlier this year, new AI travel startup Tripnotes launched its “generative” model to help travelers plan their ultimate travel itinerary and maximize the most of their time. This technology offers an interesting starting point, to which intrepid travelers can add a “more personal, human touch.”

Just this week, KAYAK rolled out a holiday version of its popular Best Time To Travel Tool. The tool supposedly has over 8,000 routes worldwide that travelers can test to see when to book and find the cheapest days to fly for a four-day, seven-day, or 14-day trip. The tool promises to be as simple as entering your home airport, final destination, and length of travel. In return, KAYAK will theoretically recommend the cheapest days to depart and return for your holiday trip, even going as far as recommending the best time to book for the cheapest price.

This sounds great…in theory. Yet when we went ahead and tried it for six different routes, we kept getting an error message and were informed the tool “didn’t have sufficient data” to supply us with what it promised.

According to KAYAK’s website, the tool uses data derived from KAYAK’s internal historical searches for the winter holiday travel period, encompassing departure dates between December 15th to December 31st and return dates between December 26th to January 8th. Additionally, flight price forecasts are estimated based on KAYAK’s analysis of current and historical minimum roundtrip prices for a single travel in economy class, taking into consideration the projected departure and return dates.

Having lived in four states over four years, I’ve had my fair share of holiday travel difficulties trying to make it back home. To test out the tool, I tried plugging in my current home city of Asheville, NC to get some data on when to fly home to my Western New York hometown. Unfortunately, I was met with a dead end with no data available.

While annoying, it could make sense considering Asheville is only a small, regional airport.

I tried this for my previous home bases in Denver, CO, and Salt Lake City, UT, as over the years it was incredibly hard to secure a holiday flight for anything less than $600. I was still met with a dead end, which is troubling considering all three are international airports.

So what’s the catch here?

Basically, while it looks good on paper, the tool seems to lack quite a bit of what the common folk need to… actually use it. Most of its 8,000 routes come from the large airport hubs of Los Angeles, New York, Chicago, and Miami. While these are great, many people aren’t necessarily flying into these cities to spend time with their families for the holiday season. There are definitely a lot of gaps and the tool doesn’t seem ready to be fully utilized by as many prospective holiday travelers as KAYAK might assume.