Kayak and Expedia develop AI travel agents inspired by social media
Kayak and Expedia are pioneering AI travel agents that transform social media posts into personalized itineraries, reshaping trip planning.
Image Credit: Michael O'Donnell

Travel planning is undergoing a revolution as Kayak and Expedia leverage AI to create agentic travel assistants capable of turning social media inspiration into full itineraries. At VB Transform, executives from both companies highlighted how AI is reshaping the industry.
From Social Posts to Bookable Trips
- Expedia launched Trip Matching, a feature that converts Instagram Reels into personalized itineraries for U.S. users.
- Kayak introduced Kayak AI, a chat-based tool combining ChatGPT with flight/hotel search capabilities.
The Balance of Control
- Ramana Thumu (Expedia CTO): Emphasized the need to balance traveler autonomy with AI recommendations.
- Matthias Keller (Kayak CPO): Stressed AI's role in simplifying complex queries (e.g., finding hotels with infinity pools).
Why It Matters
- Personalization: AI can suggest activities based on weather or past preferences.
- Data Advantage: Expedia’s 30-year database and Kayak’s partnerships (e.g., former Alexa integration) fuel these innovations.
- Snackers: AI helps casual browsers by reducing friction in trip planning.
"We are striving for a travel agent that is always available, agentic, and powered by AI," Keller said.
For more on enterprise AI trends, visit VB Transform.
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About the Author

Michael Rodriguez
AI Technology Journalist
Veteran technology journalist with 12 years of focus on AI industry reporting. Former AI section editor at TechCrunch, now freelance writer contributing in-depth AI industry analysis to renowned media outlets like Wired and The Verge. Has keen insights into AI startups and emerging technology trends.