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 n

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