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Booking Holdings announced the launch of Lola, a standalone AI travel assistant created by Kayak co‑founders Steve Hafner and Paul English. The service, described as an “AI‑first OTA,” will operate as a separate product rather than a inside Booking.com. Hafner reported that a team of about 20 engineers and product staff in New York and Cambridge spent five months building Lola from scratch, using fresh code and branding under a “greenfield” mandate from Booking Holdings CEO Glenn Fogel. Lola is positioned to answer open‑ended travel queries—such as “What should I do this weekend?”—and guide users through the entire booking process via a conversational interface.
Booking Holdings, the parent company of brands like Booking.com, Priceline and Kayak, introduced Lola on Tuesday, September 30, 2026. The announcement was made through an exclusive interview with Skift, which highlighted the product’s purpose as a conversational travel assistant that can take a user from an open‑ended travel idea to a confirmed reservation in a single chat session.
The assistant was conceived by Kayak co‑founders Steve Hafner and Paul English, who now lead the Lola team as a wholly owned subsidiary of Booking Holdings. Hafner reports directly to CEO Glenn Fogel, who gave the team a “greenfield” mandate to build the product from the ground up, allowing the use of fresh codebases and distinct branding separate from existing Booking.com features.
According to Hafner, the Lola team consists of roughly 20 employees split between New York and Cambridge, Massachusetts, and has been developing the assistant for five months. The product is not an add‑on to Booking.com but a separate AI‑first online travel agency (OTA) that aims to simplify the travel planning process through natural‑language interaction.
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Lola represents a shift in how online travel agencies may engage customers, moving from traditional search‑and‑filter interfaces to conversational AI that can handle end‑to‑end itinerary planning. If successful, the assistant could lower friction for travelers, increase conversion rates for Booking Holdings, and pressure competitors to develop similar AI‑driven experiences. The product also illustrates how large travel conglomerates are leveraging startup‑style agility—granting a small, focused team access to corporate resources—to accelerate AI innovation. However, the rollout raises questions about data privacy, model transparency, and the potential for AI‑generated recommendations to travel choices.
The launch underscores a broader industry trend toward AI‑centric consumer experiences, where conversational agents replace traditional UI elements to reduce decision fatigue and streamline transactions. By handling the entire booking workflow, Lola could improve conversion rates and increase average order values for Booking Holdings.
Lola’s positioning as a standalone OTA rather than a within an existing platform suggests a strategic move to create a differentiated brand that can experiment more freely with AI capabilities, pricing models, and user experience designs without the constraints of legacy systems.
The initiative also raises important considerations around data privacy and . As Lola processes personal travel preferences and payment information, regulators and consumer advocates will likely scrutinize how the assistant stores, uses, and protects user data.
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Key indicators to monitor include Lola’s public availability timeline, pricing or subscription model (if any), integration with existing Booking.com services, user adoption metrics, and any regulatory scrutiny over AI‑driven travel advice. Competitors’ responses—such as new AI features from Expedia, Priceline, or emerging travel startups—will also shape the market dynamics. Finally, the handling of personal data and the accuracy of AI‑generated itineraries will be critical for trust and long‑term viability.
Availability: Whether Lola will be released to the general public immediately, or rolled out in a limited beta, remains unclear. Monitoring the rollout schedule will indicate the company’s confidence in the product’s readiness.
Pricing: The announcement did not disclose any subscription fees or transaction costs. Future announcements about pricing structures will be critical for assessing market competitiveness.
Integration: Observers should watch for any future integration of Lola’s capabilities into Booking.com or other Booking Holdings brands, which could amplify its reach.
Competitive response: Rival OTAs may accelerate their own AI initiatives, potentially leading to a rapid escalation of AI features across the travel sector.
Regulatory and privacy issues: Any statements from data protection authorities or consumer groups regarding Lola’s handling of personal data will be a key factor in its long‑term adoption.