Booking Holdings Runs Five AI Bets as Priceline's Penny Leads the Field

Penny, Priceline's consumer-facing assistant, has been rebuilt into an underlying agentic system and is the most visible of the group's AI efforts to date. Executives have highlighted the tool during earnings calls and financial presentations as an example of how the company is embedding AI directly into the booking journey.

Speaking at the Citi 2026 Global TMT Conference, Booking Holdings president and CEO Glenn Fogel said the early results are encouraging. "We're definitely getting good CSAT numbers," he said, referring to customer satisfaction scores, and pointed to solid engagement and higher conversion. He also cautioned that the findings rest on a very small sample.

Three of the group's brands — Priceline, Agoda and Booking.com — are each developing trip-planning tools. Agoda's version is the closest to launch, adding a further consumer touchpoint to a portfolio that spans multiple regions and booking styles.

The wider program counts five major AI initiatives, two of which are internal startups housed inside the company. That structure gives Booking room to test consumer-facing applications across several formats at once rather than betting on a single product.

Rival Expedia is taking a comparable multi-angle approach, spanning chatbots, specialized agents and startup ventures. The two companies' strategies overlap in places but differ in emphasis, reflecting how major travel platforms are spreading their AI investment across more than one route to the customer.