ChatGPT checked Kayak and found an earlier way home from Costa Rica
Booking flights for a Costa Rica trip, a picky traveler asked ChatGPT to look them up. It checked Kayak, noticed the return flights got in too late and offered other options; they ended up booking one.
Done withChatGPTSpotted· by Alexandra Zubko· Oct 21, 2026
Result More personal than Kayak's filters and buttons
“It found a bunch of flights leaving earlier from Liberia, going to Houston.”
Spotted: found in the wild. Details are as reported by the source above and have not been independently verified.
What they did
The writer, planning a trip to Costa Rica, asked ChatGPT to look up flights. ChatGPT consulted Kayak.com. It recognized that the return flights didn’t get in before the desired time and offered to look for other options.
How it went
It found a bunch of flights leaving earlier from Liberia, going to Houston, and they ended up booking a flight from Houston to NYC. The writer said they could have done the same on kayak.com but found typing or voice-to-text with ChatGPT more personal and pleasant than filters and buttons.
Try it yourself with ChatGPT
Look up flights from [origin] to [destination] departing [date] and returning [date]. I want to avoid stops where possible and the return must land before [time]. If the return flights don't fit, suggest other options such as different airports or dates. List the options with prices for me to choose from; do not book anything.
A starting prompt written by Agents in the Wild. Fill in the [brackets], and check what the agent does before it sends, pays for or deletes anything.
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