The next generation of Priceline's AI travel assistant brings Anthropic's Claude into the company's proprietary AI stack, allowing travelers to move from trip idea to booking in one conversation

NORWALK, Conn., June 3, 2026 /PRNewswire/ -- Priceline today introduced the next generation of Penny, its AI-powered travel assistant and one of the most advanced AI booking experiences in travel. Agentic by design, Penny has the ability to understand complex trip requests, evaluate real-time pricing and availability, and surface tradeoffs. Where traditional online travel search requires navigating filters, tabs and separate browser windows, Penny can take a request like, "compare flights from New York to Paris, Berlin, or Madrid for the first week of July," share options across destinations, and let travelers book their trip without leaving the conversation.

The experience is built around a live, interactive map where options surface and sharpen as the conversation evolves. A preference layer combines traveler behavior with stated preferences travelers choose to share, helping Penny distinguish between what someone has done before and what matters for this trip, from budget and location to loyalty and trip purpose. Penny is designed with privacy in mind, giving travelers visibility and control over the data it can access, a foundation for the trust required as AI moves from assistant to agent.

Penny also brings a point of view to the options it surfaces, helping travelers move beyond what is available to what is most relevant. Penny's Pick highlights Penny's top recommendation across hotels, flights and rental cars, weighing the traveler's stated preferences, the context of the conversation and overall value. Penny's Take goes deeper on a single property, offering a candid read on why a hotel best fits the trip and the details worth knowing before booking. Penny's Take is in beta for hotels and will expand across the platform over time.

Penny runs on Priceline's proprietary AI stack, bringing together preference learning, memory, deals technology, and leading AI models. The result is a multi-modal planning experience where conversation, maps, recommendations and real-time travel inventory work together as travelers build their plans. The latest Claude models support core conversational reasoning and planning, marking Priceline's first Anthropic integration into a consumer-facing product. Google Cloud and OpenAI also support capabilities across search and voice. These systems connect Penny to real-time travel inventory from thousands of partners in more than 100 countries and decades of Priceline booking data. Through AI-powered translation, Penny now also converses in multiple languages, meeting travelers in the language they think and plan in.

"Our conviction from the start was that the real advantage in AI travel would not come from the model alone, but from connecting it to the context, inventory and deals that make travel bookable," said Sejal Amin, Chief Technology Officer, Priceline. "By starting Penny at more complex problems in travel booking and building outward into search, maps, preference learning and this new experience, we've designed a system that understands why a traveler makes a choice and can carry that understanding from one trip to the next."

Priceline was one of the first major travel brands to put an AI agent directly in front of customers, starting with some of the points of greatest friction in travel: checkout and customer care. That decision gave Penny a foundation in the moments closest to booking, where travelers indicate what information they need, what questions slow them down and what helps them move forward. Today, Penny operates as a coordinated system of more than 10 specialized agents that support everything from hotel search and recommendations to flights, rental cars, and customer service.

That foundation is already translating into results. In early testing, the subset of travelers who engage with Penny have shown stronger engagement and higher conversion than those who do not, while increased Penny usage has helped reduce customer support contacts. Priceline has estimated that travelers who used Penny saved an average of nearly ten minutes per trip compared with those who called customer support. A 2026 Evercore ISI analysis also found that Priceline Penny delivered the strongest end-to-end booking experience among the AI travel tools it tested.¹ The next generation of Penny builds on that momentum, advancing Priceline's role in Booking Holdings' broader vision of the Connected Trip, where every element of travel, from inspiration to the return home, works together seamlessly on behalf of the traveler.

"The value of AI in travel comes from connecting models to the real context of inventory, deals, and trip purpose," said Guillaume Princen, Head of International - Technology Companies, Anthropic. "Penny pairs that foundation with Claude's frontier capabilities in reasoning and agentic problem-solving to handle complex decisions that turn an idea into a booked trip."

"Travel planning has always been the hardest part of a trip. It doesn't have to be," said Cobus Kok, Vice President, AI Experiences, Priceline. "The next generation of Penny is built around a simple idea: describe the trip you want, and Penny handles the rest, helping travelers understand their choices, book with confidence and get to the trip they want faster."

To see Penny in action, watch the demo at youtube.com/priceline. Travelers can experience the next generation of Penny at priceline.com/penny.

About Priceline

Priceline, part of Booking Holdings Inc. (NASDAQ:BKNG), has been helping travelers get better deals for more than 25 years. Using proprietary technology to analyze billions of data points, Priceline unlocks savings across hotels, flights, rental cars, cruises, vacation packages, and more. With inventory from trusted travel brands in more than 110 countries, 24/7 customer service, Priceline VIP, and Penny, its AI-powered travel assistant, Priceline helps travelers save smarter and book with confidence. No one deals more deals than Priceline.

¹ Evercore ISI, "The Agentic OTA Opportunity?," March 24, 2026.

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SOURCE Priceline

Priceline's Penny Goes Fully Agentic