Two of the world’s leading travel platforms, Kayak and Expedia, are accelerating the development of AI-powered travel agents designed to convert social media inspiration into actual travel itineraries. Speaking at VB Transform, executives from both companies shared how agentic AI is reshaping the way people discover and plan their trips.

Kayak’s Chief Product Officer, Matthias Keller, unveiled Kayak AI, a chat-based travel planning tool that merges the power of ChatGPT with dedicated tools for flights, hotels, and web search. The platform aims to function as a 24/7 intelligent travel assistant capable of personalizing trip planning and handling complex logistics effortlessly.

“We envision a fully personalized experience that does all the heavy lifting for travelers,” said Keller, highlighting that Kayak has been experimenting with AI features for years, including earlier collaborations with Amazon Alexa.

Meanwhile, Expedia’s CTO, Ramana Thumu, emphasized the importance of balance between AI-driven automation and user control. He introduced Trip Matching, a new feature that allows U.S. customers to send public Instagram Reels of travel destinations to Expedia, which then builds a personalized itinerary based on the content.

This innovation taps into growing travel inspiration from social media, where platforms like Instagram heavily influence booking decisions. Thumu credits Expedia’s 30-year data archive for enabling this level of customization, adding that AI can also adjust plans in real time, such as suggesting activities based on forecasted weather during a traveler’s stay.

Both platforms are also using AI to assist “snackers”—users who browse without a clear booking intent—by simplifying search results and even nudging them toward booking with curated suggestions.

As AI becomes more agentic and intuitive, platforms like Kayak and Expedia are redefining the travel planning experience—making the journey from social feed to boarding gate faster, smarter, and more personalized than ever.