Kayak, the aggregator for flights, stays, and rental cars, launched Kayak.ai back in April 2025. Given the length of time it’s been in operation, I was expecting a more capable experience, but the end result, well… if it were a hotel, I’d have checked out before the sun went down on the first night.
In all fairness, it’s still in a public beta test. I’d say it’s a given that it’ll get better, but the missteps right now are too great to ignore. Here’s a brief conversation I had with it on August 27. My bolded queries are reproduced here verbatim.
the conversation
I’m looking for historic hotels in Quebec City in mid-December for a five-night stay. I don’t want to spend more than $80 per night because I’m a cheap SOB.
“Unfortunately, most historic hotels tend to be priced above $80 per night, and the lowest-priced options I found are around $105 total for the stay, such as The International House Hostel.”
Well, that just doesn’t make much sense. Taking a quick look at Kayak’s non-AI search results, there were plenty of hotels for under $80 per night in Quebec City. Maybe it was the criteria for historic hotels that were tripping up Kayak’s AI.
Ok, nix the historic hotel part.
“I found several budget-friendly options in Quebec City for your stay from December 15 to December 20. The prices are all under $80 for the entire five-night stay, but please note that some listings may be close to or slightly above this budget.”
Then it listed several hotels that were all over $100 for the entire five-night stay. I don’t blame it, because five nights for under $80 in Quebec City would be looney. But it didn’t seem to know what it was saying.
Also, I noticed that although I’d given it a purposefully vague timeframe of mid-December, it was being too rigid with the dates.
I see that you’re being very literal when I say “mid-December” and looking exclusively at stays that begin on December 15. I’m not being that particular on the day, just giving a general time range. Can you widen your range of dates to find the best rates?
“You got it—mid-December in Quebec City is running about $172 total for a five-night stay (so, around $34 per night on average).”
Then, nothing. No lists of hotels.
All righty. So… how about those listings now?
“The most affordable options in Quebec City from December 10 to 15 are mostly hostels and budget accommodations. The lowest-priced stay is around $105 at The International House Hostel, which offers free cancellation and has a decent review score of 7.1.”
Nice touch with the mention of free cancellation and the review score, but again Kayak AI got very rigid with the dates it was searching, only looking for stays that begin on December 10. Also, it was clear that Kayak wasn’t listening to my stipulation to search for hotels less than $80 per night.
Ok, so I said $80 per night maximum, not $80 for the entire five-night stay. I’m not that cheap, Jesus. Can you give me a new list following the directions correctly this time? Also, exclude hostels. I don’t like strange people staring at me three inches from my face while I sleep.
“I apologize for the misunderstanding. I have now filtered the results to exclude hostels and focused on properties with a maximum of $80 per night, which means up to $400 for the five-night stay.
“Unfortunately, there are no options available within that budget for this date range. The lowest-priced accommodations are still above your budget, starting at around $105 for the entire stay. If you’d like, I can look for alternative options or adjust the criteria further.”
Oh, boy.
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