Kayak pivots from search to AI-driven travel assistant

The shift from browsing to delegating marks one of the most significant evolutions in digital travel since the rise of OTAs – one driven not by new interfaces, but by AI that reasons, reacts, and books

May 23, 2025

As artificial intelligence reshapes industries, travel is entering a transformative era where agentic AI is set to replace traditional, static booking interfaces with dynamic, conversational planning. Companies like Kayak are pioneering this shift with tools like Kayak.ai – a ChatGPT-style assistant tailored for travel – signaling a future where users interact naturally with AI to handle everything from inspiration to bookings. This evolution promises to remove friction, personalize experiences, and eventually enable autonomous trip planning, especially in high-frequency sectors like corporate travel.

Key takeaways

From chatbot to travel partner: Kayak.ai isn’t just a chatbot – it’s a generative AI tool that enables users to ask travel-related questions conversationally and book real-time, integrated options without using traditional filters or menus.
Agentic AI drives next-gen travel planning: Rather than only surfacing results, agentic AI performs tasks for the user, including searching, refining, and eventually booking – setting the stage for seamless, semi-autonomous travel management.
Step-by-step automation rollout: While current bookings still require manual confirmation and payment entry, Kayak is moving toward systems where trips could be booked in the background with saved user data.
Corporate travel as innovation testbed: With its repeatable, high-frequency needs, corporate travel offers an ideal environment to trial advanced AI capabilities, including real-time changes and itinerary reasoning.
Privacy and security as foundational pillars: Kayak emphasizes that its deep experience in secure transactions positions it well to manage the risks associated with automated travel bookings, including handling loyalty programs and payment credentials.
Toward a truly personalized travel agent: The ultimate goal is for users to input broad goals (e.g., “three weeks in Europe for $3,000”), and the AI returns an optimized, bookable itinerary – no micromanaging required.
Future outlook: Kayak envisions transitioning from a search platform to a true AI-powered travel companion, where complex trip planning is delegated entirely to digital agents that understand user preferences and constraints.