Hilton's AI Planner Held 18,000 Guest Chats. Only 2% Would Let AI Book

Hilton's AI trip planner has held more than 18,000 conversations with guests as of August, yet only 2% of leisure travelers would let AI book a trip for them. That gap defines the hotel giant's biggest technology bet this year.

Tell the tool you want a winter getaway, and the Hilton AI Planner hands back a destination, a hotel and a plan for the whole trip, according to PYMNTS. Orlando, Aspen and the Caribbean rank among the top searches. The tool runs on Anthropic's technology.

Why does Hilton want AI in the booking flow?

The goal is keeping travelers off Booking.com, Expedia and newer booking upstarts like Uber. Every room booked through a travel site means a cut for the middleman. That economics matters most to the franchisees who run Hilton hotels.

Hilton starts from a strong position. More than 80% of its business is already direct, according to the company. CEO Chris Nassetta frames AI as a way to widen that margin of independence. He calls it "code for continuing to build more direct lines to our customers."

The company isn't limiting itself to its own channels. Hilton also shows up in Google's AI Mode and in ChatGPT, meeting travelers where they already ask questions.

Do travelers actually trust the chatbot?

Not yet. PYMNTS reports that just 2% of leisure travelers would let AI complete a booking on their behalf. Hilton's own trends report puts the trust deficit in sharper relief: only 22% of travelers trust AI to build a personalized itinerary, while 70% trust hotel staff.

The numbers suggest guests will use AI for ideas but not for transactions. They'll take a suggested destination from a chatbot. They still want a human — or at least their own click — confirming the reservation.

Nassetta himself isn't predicting a breakthrough. "I don't see that the whole system changes in a material way anytime soon," he said on Hilton's April earnings call.

What's the so-what for the industry?

The 18,000 conversations prove demand for AI-assisted planning exists. The 2% booking-trust figure proves it hasn't converted into AI-handled transactions. For now, the tool's value lies in deflecting searches away from Booking.com and Expedia before a middleman ever enters the picture.

The pressure will build on both sides. If trust numbers rise, direct-booking economics improve further for Hilton and its franchisees. If they stall, the AI Planner becomes a research layer sitting on top of a booking process travelers still control themselves. Nassetta's April comment signals Hilton expects the slow path.