KAYAK Launches Ask AI, Combining Conversational Chat With Live Search Results

KAYAK launched Ask AI on Thursday, a new product that lets travelers type questions in plain language and receive live flight, hotel, and car rental results alongside the conversation. It is the first travel search tool to keep both a chat interface and a traditional results page on screen at the same time, rather than switching between the two.

The product arrives roughly six months after KAYAK introduced a natural language search experiment in October 2025. That earlier version let travelers type queries conversationally but served results separately. According to Matthias Keller, KAYAK's Chief Product Officer, users "increasingly turn to AI to begin planning, but still depend on traditional search and filters to evaluate options and book with confidence." Ask AI tries to close that gap by keeping both experiences running simultaneously.

How it works

Travelers can ask questions in plain language, such as searching for flights to a host city and hotels near a venue, and refine the trip through follow-up messages as results update live. There is no need to restart searches or switch tabs. KAYAK says bookable options from its network of travel partners appear in real time as the conversation develops.

The launch is timed around demand building for the FIFA World Cup. KAYAK's internal data shows flight searches to Canadian host cities are up 12% year over year, with Toronto outpacing Vancouver at 19% versus 5%. Hotel prices across host markets have shifted considerably: up 55% in Canada, 36% in the US, and 119% in Mexico. Germany and the UK are the top international regions searching for travel to Toronto and Vancouver.

Alongside Ask AI, KAYAK is publishing a World Cup Travel Trends Dashboard, a publicly accessible page drawing on KAYAK's real-time search and pricing data to track demand movements across the 16 host cities in Canada, the US, and Mexico.

What this means for accommodation operators

The pricing data KAYAK released alongside the product is the most immediately useful number in this announcement for operators. A 55% increase in average hotel rates in Toronto and Vancouver is a steep shift. If those figures reflect actual market rates rather than search-based projections, properties in Canadian host cities may still have room to adjust pricing for summer as demand continues building closer to kickoff.

The broader question is how a shift toward AI-mediated discovery changes visibility for individual operators. In conventional metasearch, properties compete on rate and availability that travelers can see and compare directly. In a conversational interface, ranking within the chat is less visible. KAYAK has not disclosed exactly how Ask AI surfaces accommodation options within a session. That is worth monitoring as the product gains users.

Ask AI is live now on KAYAK's Canadian platform.