Kayak and Expedia race to build AI travel agents that turn social posts into itineraries

When people started to talk about AI agents and assistants, the number one use case revolved around travel. Could someone be watching a video about the Maldives and direct their AI agent to start finding flights and hotels, and book these seamlessly? 

We‘re inching closer to a similar future as the travel industry begins to embrace agentic AI. Kayak and Expedia, two of the largest companies in travel booking, said during VB Transform that personalization and changing search patterns mean travel companies can rely on agents to make travel inspiration a reality.

Matthias Keller, chief product officer at Kayak, said the company has been experimenting with this idea for a couple of years, even taking advantage of a partnership with Amazon’s Alexa. Kayak no longer launches on Alexa, but that hasn’t stopped the company from offering different search modes for customers.

“We are striving for this vision of a travel agent that is always available, that is agentic and powered by AI,” Keller said onstage at VB Transform. “In April, we launched our new testbed for agentic travel booking called Kayak AI; it’s a fully chat-based agentic experience that puts together the power of ChatGPT and many different tools. One is web search, but we also offer tools specifically for flights or hotels.”

Keller said Kayak is “working towards our vision of having this fully personalized experienced that does all the heavy lifting for you when you plan travel.”

While the idea of an agent proactively guiding potential travelers makes for efficient trip planning, Expedia CTO Ramana Thumu noted that there is a delicate balance to strike.

“More and more customer expectations will revolve around a seamless experience, from search to completing transactions,” Thumu said. “But the most important thing, and the shift I see happening, is asking for the balance between the control the traveler has, and the control we give to the agent.”

One reason this balance becomes essential is that, increasingly, consumers find travel inspiration everywhere. For one of its AI projects, Expedia decided to capitalize on the growing influence of travel influencers who post their trips on Instagram.

Thumu said Expedia’s Trip Matching feature, which launched in June for U.S. customers, allows people to send any travel-related public Instagram Reel to Expedia, and the platform can build an itinerary based on them. 

Thumu said Expedia can build this type of AI product because of its extensive database amassed over 30 years. Both Thumu and Keller underscored the importance of data in building out these personalizations, a task that can be challenging. 

Personalization can go beyond planning a trip based on inspiration or previous preferences, as Keller said; eventually, their platforms and AI agents can also start recommending things to do based on the weather in your planned location during your stay. 

AI helps simplify the complexity

One use case where companies like Kayak and Expedia find AI to be helpful is for “snackers,” or individuals who search for flights or hotels without any intention of booking. These are usually people who just want to check the price of a flight or find out how much a hotel costs. 

AI systems can help snackers find their answers, and may even encourage them to go on that trip, because much of the tediousness of finding accommodation, transportation and activities can be presented to them right there on either the Expedia or Kayak front end. 

“What I find interesting when I pitch Kayak AI to somebody [is] I can say that we can get this complex trip planned without running all of the searches,” Keller said. “Every hotel booking site out there can tell you that a hotel has a pool, but you have to go deep to find an infinity pool. That’s the type of question that ChatGPT does a great job with, so it’s something we have to adapt and deliver.”