The internet has repeatedly changed how people travel. First came the browser, then smartphones. Each shift promised to flatten the industry further, cutting friction, shrinking the role of middlemen, and pushing more of the experience into software. But AI introduces a different possibility entirely: What happens when people stop visiting travel websites at all?
Few companies have lived through every phase of that evolution quite like Expedia Group.
The company survived the rise of Google, the collapse of desktop computing, the mobile revolution, platform monopolies, and a pandemic that temporarily froze global travel. For decades, Expedia controlled nearly the entire customer journey inside its own ecosystem: discovery, booking, loyalty, customer support, payments. AI agents threaten to break that apart, scattering pieces of the experience across chatbots, recommendation engines, and autonomous assistants.
Founded inside Microsoft in 1996 by Rich Barton, Expedia was built around a simple idea: ordinary people should be able to plan and book travel themselves instead of relying on agents or opaque reservation systems. “I understood early that people love control. Expedia didn’t have business hours because the web never closes,” Barton tells Fast Company. “The biggest hurdle back then was getting people to trust their credit cards on the internet.”
He sees AI producing a similar moment now. The challenge, he argues, is less technical than psychological. “We’ve been here before,” he says. “Every single time, we worked through the fear and incorporated it into our lives, mostly for the better.”
The major transition came under former CEO Dara Khosrowshahi, now CEO of Uber, as smartphones fundamentally changed how people booked trips. Expedia responded by consolidating scale, acquiring Orbitz, Travelocity, and HomeAway.
Now comes yet another transition, one where travelers increasingly begin planning somewhere other than a travel site. They ask chatbots for hotel recommendations. They build itineraries through natural-language prompts. They use AI tools to compare destinations, prices, and routes. But Expedia executives think much of Silicon Valley may be misunderstanding something important: generating inspiration is not the same thing as handling transactions.
“The future belongs to platforms that deliver trust, fulfillment, and accountability,” says Expedia CEO Ariane Gorin. “Two-thirds of our bookings come from people who come directly to us. ChatGPT, Gemini, Google, wherever it may be, we’re going to make sure our brands show up well there.”
The anxiety hanging over the industry is fairly obvious: travel brands risk becoming invisible infrastructure underneath somebody else’s interface. Gorin says Expedia is now in its “third chapter,” trying to adapt itself for AI systems without losing the operational machinery it spent decades building.
“We are revisiting everything on our platform to ensure all capabilities are AI-readable,” she says. “Our advantage is 30 years of deep expertise and knowledge in the travel industry.”
Travelers Use AI for Planning But Not Booking
Expedia’s own “AI Trust Gap” report captures the contradiction facing the industry. Travelers are increasingly comfortable using conversational AI to brainstorm trips, monitor prices, and surface destinations they otherwise might never have considered.
Actually handing over money is another matter. Nearly 68% of travelers say they would rather book through established travel companies than AI chatbots. Two-thirds say they would not trust an AI assistant to purchase or book something on their behalf. Just 8% say they feel comfortable booking directly through an AI platform. “Consumers don’t want to hand over control for stuff they care about—they want to feel more in control,” Barton says.
He describes the ideal AI assistant less as an autonomous travel agent than as “a brilliantly prepared friend in your corner,” somebody who has already done the research and narrowed the options without making the decision for you.
“You’re still deciding,” Barton says, “but you just have a much better foundation to decide from. That’s meaningfully different than ‘the algorithm picked this for you.’”
That distinction matters in travel because operational trust tends to reveal itself only when things go wrong. Flights get canceled. Hotels overbook. Refunds stall. A third of travelers in Expedia’s survey worried about customer service failures tied to AI booking systems. Others cited concerns over privacy, payment security, and loss of control.
“Trips are not like T-shirts,” Gorin says. “If something goes wrong, you’re not going to get that time back.”
Expedia operates consumer brands including Expedia, Hotels.com, and Vrbo, but much of its business sits deeper in the travel stack. Airlines, hotels, banks, loyalty programs, and other partners rely on Expedia’s infrastructure for inventory, booking systems, rewards integrations, and distribution. The company has also accumulated decades of traveler data, roughly 70 petabytes worth.
That operational depth may matter more in an AI economy than many startup founders assume.
“Our consumer brands may be less than 10% of the global travel market, but our B2B business can power all the rest,” Gorin says. “We get to participate in the entire ecosystem because we have both B2C and B2B. We don’t see what other people are doing as a threat.”
Own the Fulfillment, Not the Interface
Last month, Uber announced a partnership with Expedia allowing users to book hotels directly inside the Uber app while integrating Uber rides into Expedia’s travel ecosystem.
The deal reflects a broader shift already underway: travel increasingly behaves less like a destination website and more like embedded infrastructure. “Uber is becoming an app for everything,” Khosrowshahi says in a statement to Fast Company. “What excites the company about this partnership is a shared belief that travel should feel more connected.”
Expedia appears increasingly comfortable with that possibility. Gorin repeatedly frames the company as infrastructure sitting underneath a fragmented travel ecosystem. “We get to power the ecosystem and be the plumbing,” she says. Right now, AI-driven traffic still represents a tiny slice of Expedia’s business, less than 1.5%, according to Gorin. But the company expects that to grow quickly as conversational interfaces reshape how people search and plan trips.
(Even as Expedia increasingly positions itself as infrastructure, the company is still trying to maintain a consumer-facing travel identity. It recently launched the Expedia Trails Fund, a $4.3 million conservation initiative supporting parks, trails, and coastlines through partnerships with groups including The Nature Conservancy and Trust for Public Land.)
The broader bet is that ownership of the customer interface may ultimately matter less than ownership of the systems underneath it. AI startups can generate itineraries quickly. Handling refunds, payments, inventory management, loyalty programs, multilingual servicing, and customer support at global scale is harder.
That may complicate one of Silicon Valley’s favorite assumptions: that technological revolutions naturally favor startups over incumbents.
“The companies that will be successful are companies who have a clear purpose and understand what travelers want, how to deliver it,” Gorin says.
Whether that turns out to be true is still unclear. AI may weaken the importance of travel brands altogether, turning booking platforms into interchangeable back-end utilities beneath more powerful consumer interfaces. Or it may strengthen the companies that already own the messy operational systems required to actually move people around the world.
Either way, the travel industry appears headed toward another restructuring, one where the battle may no longer be over who owns the homepage, but who owns the fulfillment layer underneath it.
Startups Won’t Disrupt Travel Like Silicon Valley Thinks
Silicon Valley tends to assume technological revolutions favor startups over incumbents. But AI may produce a stranger outcome in industries built on operational trust. Airlines still need integrations. Hotels still need distribution. Travelers still need refunds, loyalty programs, customer service, and accountability when trips fail. Those systems do not disappear just because the interface changes.
“The companies that will be successful are companies who have a clear purpose and understand travelers—what they want, how to deliver it—and have the whole organization line up behind it,” Gorin says. Since becoming CEO, she has reorganized the company around “Serve the Traveler,” while pushing teams to use Expedia’s own products through an internal Dogfood program designed to expose operational weaknesses faster.
Technology may solve much of travel’s complexity, Gorin says, but only if it stays connected to the traveler experience. “If you can look at the product and say, ‘This is valuable to travelers,’ then you’ll be fine,” she adds.
Her three strategic priorities reflect that philosophy: “Create more traveler value, invest where there’s growth, and drive margin expansion while making every dollar count.”