Booking Holdings is preparing a new move in AI-powered travel with Lola, a startup project that reunites Kayak co-founders Steve Hafner and Paul English under one of the industry’s largest online travel groups. The project signals how quickly major travel platforms are shifting from traditional search boxes toward conversational tools that can interpret traveler intent, suggest options, and potentially complete more of the booking journey inside a single interface.
Lola is expected to build on the brand originally launched by English as a travel startup before later shifting into business travel and expense software. That earlier company became known for combining travel booking with human support and software tools for corporate users. The new version appears to be moving in a different direction, with the Lola.com and Lola.ai domains now connected to Booking Holdings and positioned around “insider access” to major travel brands.
The early messaging suggests a consumer-facing product built around conversational AI. Rather than asking users to filter through multiple tabs and booking pages, Lola may allow travelers to ask for better rates, options, and access across participating brands. SeatGeek has been listed among partners, while the broader Booking Holdings ecosystem includes major travel names such as Booking.com, Priceline, Agoda, Kayak, OpenTable, and Rentalcars.com.
For Booking Holdings, the project arrives at a moment when online travel agencies are under pressure to defend their role in the booking funnel. Generative AI tools from large technology companies have already changed how consumers search for information, and travel is one of the categories most exposed to that shift. If travelers increasingly begin with AI assistants rather than search engines or metasearch sites, platforms such as Booking Holdings need their own products that can keep users inside their networks.
The involvement of Hafner and English gives Lola additional weight. Kayak helped define metasearch for a generation of online travelers, making it easier to compare flights, hotels, and rental cars across providers. Reuniting the founders around an AI product suggests Booking Holdings sees the next major interface shift as strategically important, not just experimental.
The timing also reflects a broader industry race. Travel brands are testing AI agents, itinerary assistants, customer service bots, and personalized booking tools, but many products still struggle to move from inspiration to transaction. Lola’s challenge will be turning conversational discovery into something reliable enough for real bookings, pricing, customer support, and partner distribution.
If successful, Lola could become a new front door for Booking Holdings, especially for travelers who want fewer steps and more tailored options. It also revives a familiar travel tech name at a very different moment, when the next competitive advantage may come less from search results and more from how well a platform can understand a simple request.