KAYAK launches Ask AI to simplify travel planning

KAYAK has unveiled Ask AI, a conversational planning interface aimed in particular at travellers preparing for the 2026 World Cup. The new AI-powered search and trip-planning experience lets users chat in natural language while live flight, hotel and car-hire results update alongside the conversation. The company, which is part of Booking Holdings, frames the launch as a response to increasingly complex booking journeys, especially for a tournament spanning the United States, Canada and Mexico. KAYAK is also introducing a World Cup Trends Dashboard to track shifting interest, prices and the destinations gaining the most momentum.

An assistant linked to tournament data

Ask AI lets travellers issue an open request, then hone their criteria progressively as the chat evolves. Users can, for instance, ask for a hotel near a stadium, compare flights between multiple host cities or build an itinerary that combines transport, accommodation and car hire without starting a new search at every stage. Results show up-to-date prices and bookable options from hundreds of travel partners. The accompanying dashboard adds a decision-making layer by aggregating demand signals, price pressure and the destinations whose appeal is rising as the event approaches.

According to KAYAK, flight searches to U.S. host cities are up 23% year on year over the summer period. Some destinations are seeing standout spikes, notably Kansas City, where flight searches have risen 168% year on year. Hotel prices are climbing across all three host countries, with increases of 36% in the United States, 55% in Canada and 119% in Mexico.

The tool primarily targets travellers planning trips around the 2026 World Cup, but more broadly anyone who wants to move from a natural-language prompt to a bookable itinerary. Beyond the tournament, its ambition is as much commercial as it is ergonomic: provide guidance at the inspiration stage, support trade-offs, and keep the transaction within a single environment.

"After launching our first natural language search experience in October, we saw that travelers increasingly turn to AI to begin planning, but still depend on traditional search and filters to evaluate options and book with confidence," said Matthias Keller, chief product officer at KAYAK. "Ask AI is the next evolution, combining both in a single, seamless user experience."

For context on the October rollout, see the launch of KAYAK's first natural language search experience.