Kayak's AI Mode and the Natural-Language Pivot in Metasearch

For travel professionals watching metasearch, Kayak's AI Mode is the clearest signal yet of how intent-driven queries are reshaping the category. Launched in October 2025 and now available to all users, the feature points to a broader shift: travelers are no longer starting every session with a fixed destination and dates.

What shipped

Kayak rolled out AI Mode on 15 October 2025, introducing a conversational search layer that pairs the metasearch engine's own data with ChatGPT. Users click the "AI Mode" icon on Kayak's website from a desktop or mobile browser and type queries the way they would speak them, rather than filling in preset entry fields. Behind the scenes, Kayak compares prices and availability across travel providers in real time and returns bookable options in the same interface.

The feature was positioned alongside earlier AI experiments that Kayak had already placed in market, including Kayak Price Check — which reads flight fares from a screenshot — and Ask Kayak, the company's first conversational interface.

The Kayak.ai connection

AI Mode is the first feature to graduate to Kayak's main site from Kayak.ai, a separate "test lab" that Kayak launched in April 2025. The company has described Kayak.ai as the place where its engineers experiment with cutting-edge capabilities before deciding which ones reach mainstream travelers.

"We launched Kayak.ai in April for our software engineers to test cutting-edge AI capabilities. AI Mode is the first feature to graduate to our main site," Kayak CEO Steve Hafner said at launch. "Travelers aren't limited to preset entry fields anymore. Just tell us what you're looking for in plain language, and we'll answer the same way."

Why it matters

The launch lands at a moment when every major OTA is trying to stay relevant as travelers increasingly start planning with large language models instead of traditional search boxes. Kayak's bet is that structured price comparison stays central even as chat-style interfaces absorb more of the inspiration stage of trip planning. AI Mode is how that bet shows up inside the product: conversational intake at the top of the funnel, structured comparison at the bottom.

For hotels and OTAs that rely on Kayak as a distribution channel, the shift from structured forms to conversational queries changes both what travelers ask for and when in the planning cycle they arrive. Early signals from Kayak suggest users engaging with AI Mode are much more likely to start without a fixed destination or dates, leaning on broad, intent-driven prompts instead.

End of an era

AI Mode is one of the last headline launches of Hafner's 22-year run. In February 2026, Skift reported that Hafner is stepping down as Kayak CEO after more than two decades at the helm. His successor inherits a product that is already being studied closely as a bellwether for how intent-driven AI search will reshape the economics of metasearch — and a test lab in Kayak.ai that is purpose-built to keep shipping whatever comes next.