Booking’s big AI gamble: Beating ChatGPT at its own game

Why the travel giant thinks travelers will trust its “Connected Trip” AI more than Silicon Valley’s bots

Booking wants you to imagine a future where your itinerary basically builds itself. Flights delayed? Your car rental shifts automatically, with a child seat already installed because the system remembers you’re traveling with your toddler. Hotels show up with parking spots included. Attractions slot into your schedule without you lifting a finger. That’s the “real connected trip” Booking’s CFO Ewout Steenbergen pitched this week — powered not by ChatGPT or Google Gemini, but by Booking’s own agentic AI.

Key takeaways

• Agentic AI with teeth: Booking isn’t just answering questions — it’s building an AI that books, rebooks, and connects the dots across travel.
• Trust over hype: Steenbergen says travelers will prefer a Booking-branded AI that comes with accountability when things go wrong.
• Connected trip dream: The endgame is a fully personalized itinerary that updates in real time, giving travelers “peace of mind.”
• Cheaper service, happier guests: AI tools are cutting customer service costs and lifting satisfaction, with natural language search reducing cancellations.
• Pricing model catch-up: Short-term rentals are adopting Booking’s all-in pricing approach, ditching surprise fees and leveling the field with Airbnb.
• Airbnb who?: Booking’s alternative accommodations have outgrown Airbnb in 16 of the past 17 quarters, now making up over a third of room nights.

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