Trending Now - Expedia Evolves Beyond Travel Sites as it Marks 30 Years

WHO:

Fast Company - Expedia Group CEO Ariane Gorin, founder Rich Barton, chairman Barry Diller, and former CEO Dara Khosrowshahi.

WHAT:

Fast Company - Expedia is preparing for a future beyond travel websites as it marks its 30th anniversary.

Fast Company - Nearly 68% of travelers prefer to book through established travel companies rather than AI chatbots.

Fast Company - Two-thirds of travelers do not trust an AI assistant to purchase or book something on their behalf.

Fast Company - Only 8% of travelers feel comfortable booking directly through an AI platform.

Fast Company - Expedia operates consumer brands including Expedia, Hotels.com, and Vrbo.

Fast Company - Expedia has accumulated roughly 70 petabytes of traveler data.

Fast Company - Expedia's AI-driven traffic currently represents less than 1.5% of its business.

Fast Company - Expedia recently launched the Expedia Trails Fund, a $4.3 million conservation initiative.

WHERE:

Fast Company - Expedia was founded inside Microsoft.

WHEN:

Fast Company - Expedia was founded in 1996.

Fast Company - Uber announced a partnership with Expedia allowing users to book hotels directly inside the Uber app.

WHY:

Fast Company - The shift towards AI in travel is driven by the need for platforms that deliver trust, fulfillment, and accountability.

Fast Company - Travelers are increasingly comfortable using conversational AI for trip planning but are hesitant to trust it for booking due to concerns over control and operational trust.

HOW:

Fast Company - Expedia is revisiting its platform to ensure all capabilities are AI-readable.

Fast Company - The company has reorganized around the philosophy of "Serve the Traveler" and implemented an internal Dogfood program to expose operational weaknesses faster.

(UPDATED May 19, 2026 23:26 UTC)

Expedia is celebrating its 30th anniversary and is preparing for a future that extends beyond traditional travel websites, as the company has reorganized around the philosophy of "Serve the Traveler." Despite the rise of AI in travel, nearly 68% of travelers still prefer booking through established companies rather than AI chatbots, with only 8% feeling comfortable making reservations directly through an AI platform. To support its evolution, Expedia has launched the $4.3 million Expedia Trails Fund, while also focusing on making its platform more AI-readable and addressing operational weaknesses through an internal program.