Booking Bets on Lola Before Chatbots Become Travel’s New Starting Line

Booking Holdings is working on a new AI travel startup called Lola with Kayak co-founders Steve Hafner and Paul English.

The product appears to focus on conversational travel planning, where users ask for trip options, deals, and recommendations.

The teaser pages for Lola.com and Lola.ai promote “insider access” to major travel brands, better rates, and better options.

Lola could become a new front door for travel

Lola appears to be separate from Booking Holdings’ main brands, such as Booking.com, Priceline, Agoda, Kayak, and OpenTable. Instead of only adding AI tools to those platforms, Booking is testing a new product that could become an entry point for travel discovery.

Booking wants to protect its customer journey

Booking Holdings has a clear reason to invest in Lola. General AI assistants from major tech companies could become the first place travelers go for hotel, flight, or event recommendations. That could weaken Booking’s direct relationship with customers.

Lola gives Booking a way to keep more users inside its own ecosystem. The company already has large travel supply, well-known brands, payment tools, and customer data. A conversational AI product could make those assets easier to use.

SeatGeek is listed as a partner. This suggests Lola may connect travel with events, making it useful for trips built around concerts, sports, or entertainment.

Kayak’s founders bring travel search experience

Steve Hafner helped build Kayak into one of the best-known travel metasearch brands. He stepped down as Kayak CEO in February 2026 after 22 years and moved into an AI-focused role at Booking Holdings.

Paul English, Kayak’s former chief technology officer, is also involved part-time. He previously co-founded the original Lola in 2015 as a travel agency platform that combined software with human advisors. The company later shifted into business travel and expense management before Capital One acquired its team and software in 2021.

Now, the Lola name is returning as an AI travel project.

Lola points to Booking’s bigger AI plan

Lola has not launched as a full product yet. Its public pages are still teasers, and Booking Holdings has not shared detailed features, pricing, or a launch date. However, the company has confirmed that it is testing new generative AI initiatives, with Hafner leading some of them.

Booking is already using AI across Booking.com, Priceline, Agoda, Kayak, and OpenTable to speed up search, improve self-service, and reduce support costs. Lola could be the next step in that strategy: not just making existing travel websites smarter, but building a new AI-first entry point for travelers before they even start a traditional search.

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