KAYAK Launches Ask AI for Conversational Trip Planning in US, UK and Canada

KAYAK has rolled out a conversational AI search tool called Ask AI, making it available to all travelers in the US, UK, and Canada, with more markets planned.

The tool lets users search for travel options through free-form natural-language questions rather than structured filters. Instead of entering dates and destinations, a traveler can type something like "where can I go with family under 3 hours from NYC for less than $300 per person" and get results across flights, hotels, and car rentals at once.

Ask AI also works as a filter layer on top of standard searches. Once a user is looking at results, they can narrow options by asking for specific attributes: no layovers with the shortest flight possible, a hotel with a gym in walking distance to Central Park, a luxury sedan with airport pickup and free cancellation. The idea is to cut down the tab-opening and checkbox-clicking that typically comes with trip planning.

The feature covers all three of KAYAK's main categories. For flights it handles queries about departure time, layovers, cabin class, and flight duration. For hotels it interprets requests about amenities, room type, location, and traveler rating. For car rentals it filters by vehicle type, pickup location, and cancellation policy.

KAYAK is owned by Booking Holdings (NASDAQ: BKNG), which has been embedding AI search across its brands. The launch comes as virtually every major travel metasearch and OTA is working to shift users toward conversational search interfaces, betting that travelers who find planning easier will book more frequently and with less comparison shopping.

For accommodation operators listed on KAYAK, the shift to AI-mediated results changes the weighting logic that determines which properties appear. Detailed, accurate attribute data in a listing becomes more valuable when the search layer is parsing natural-language queries rather than matching keywords and filters mechanically.

The US, UK, and Canada rollout is a full launch after an earlier preview phase. KAYAK has not provided a specific timeline for additional markets.