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Priceline has upgraded its AI travel assistant Penny with agentic booking functionality that lets users complete trips inside the conversation. The update reflects a broader shift in online travel from search-led browsing toward more guided, transaction-ready AI interfaces.
Priceline has revived its iconic Negotiator character, with William Shatner handing the role to Randall Park in a new campaign focused on summer travel affordability.
Kayak co-founders Steve Hafner and Paul English are working on Lola, a new Booking Holdings-backed AI travel startup focused on conversational access to travel brands.
Booking Holdings reports strong 2025 results, with multi-vertical “connected trip” bookings surging and AI driving efficiency gains.
Southwest Airlines has partnered with Priceline to offer travelers more booking options, allowing customers to book Southwest flights directly on Priceline’s platform while still earning Rapid Rewards points.