#36 Expedia & Booking.com Just Moved into ChatGPT

Airbnb’s Loyalty Program

Expedia & Booking.com Just Moved into ChatGPT — and the Future of Travel Search Is Changing Fast

Expedia and Booking.com have officially launched apps inside ChatGPT, giving travelers access to live pricing, maps, and hotel inventory without ever leaving the chat. What many assumed would disrupt online travel agencies (OTAs) is instead amplifying their dominance. Nearly one-third of ChatGPT’s first app partners are OTAs, signaling that conversational AI isn’t replacing them — it’s extending their reach.

OpenAI’s new Apps SDK turns ChatGPT into a platform with 800 million potential users. Alongside Expedia and Booking.com, brands like Tripadvisor, Uber, and TheFork are also joining, creating a new distribution channel for travel discovery and booking. Users can now compare hotels, check flights, and view destinations directly through chat-based interactions — a frictionless, AI-driven version of travel search.

This evolution mirrors how travelers are already behaving: more than 70% of consumers now research trips online, using search, social, and increasingly AI tools for recommendations. The line between searching and booking is blurring.

Expedia reports that generative AI-driven traffic, though small, converts at higher rates — suggesting users who plan through AI are more decisive and ready to buy.

For OTAs, the move locks in their relevance at a time when Google’s ad dominance has squeezed margins. For hotels, however, it’s both a warning and an opportunity. As travelers turn to AI platforms for instant answers, the window for direct booking narrows — unless hotels move fast. Integrating their own AI chat tools, optimizing for conversational search, and offering loyalty-based incentives for direct booking could help reclaim visibility.

---

Airbnb’s Loyalty Program: A New Kind of Hospitality Currency

Airbnb is gearing up to launch its first-ever loyalty program, but unlike hotel giants such as Marriott or Hilton, it’s not planning a traditional points system. CEO Brian Chesky has teased that “something big is coming,” hinting at a loyalty model that reflects Airbnb’s broader transformation — from a home-sharing platform to a full-fledged travel ecosystem that increasingly includes hotels, experiences, and services.

In the past, Airbnb’s growth came from simplicity: no memberships, no tiers, just listings and reviews. But as it integrates hotels into its platform and competes for repeat travelers, loyalty has become a strategic necessity. Hotel chains have long used points programs to lock in guests and drive direct bookings — a playbook Airbnb can’t ignore if it wants to retain high-value customers.

The company’s HotelTonight pilot—offering 10% Airbnb credit on bookings—was a clear test case. Expect that to expand into a flexible system of credits, discounts, and experiential perks spanning stays, local experiences, and add-ons like private chefs or tours.

For hotels, Airbnb’s move is both a challenge and an opportunity. On one hand, it may lure guests who value flexibility over points. On the other, it opens a powerful distribution channel — if hotels can align with Airbnb’s model while maintaining brand identity and direct relationships.

The biggest implication? The definition of “loyalty” in travel is changing. It’s no longer just about earning free nights — it’s about being part of an ecosystem that rewards how, not just where, you travel. For Airbnb, this could be its most important evolution yet — and for hotels, a wake-up call to rethink loyalty in an age where experience, not occupancy, drives repeat business.