With the Phocuswright conference days away the subject of Travel AI will be center of the plate. After decades of digitizing bookings, the travel industry is now digitizing imagination. The shift is powered by artificial intelligence—particularly agentic AI, systems that don’t just answer questions but take action on your behalf.
Expedia Group’s Chief Product and Technology Officer for B2B, Karen Bolda, says this evolution moves the industry from efficiency to anticipation: “AI can do so much more above and beyond just improving and fixing some of these inefficiencies.”
Across Skift Research, McKinsey, and conversations with Expedia, a clear consensus is emerging: by 2026, AI will redefine how travelers plan, book, and experience trips—and how brands build loyalty in the process.
From Efficiency to Imagination
Early AI applications in travel focused on automation: call-center deflection, better search results, faster rebookings. Now, the next phase of transformation is about emotional intelligence and context.
As Bolda explains, “You don’t dream about making a booking. You dream about moments.” Expedia’s Smart Trip AI, announced in 2024, brings that idea to life by merging first-party data with partner insights to generate personalized, mood-driven itineraries—like a “walkable weekend near lavender fields.”
This isn’t just user experience polish. It’s the foundation for an agentic ecosystem where AI anticipates intent, connects context, and acts. Expedia is already embedding its content and services across partner assistants—from OpenAI’s Microapps and Operator to Microsoft Copilot Actions—so travelers can move from a simple chat prompt (“show me weekend options in Santa Fe”) to a full itinerary and booking in minutes.
The Rise of Agentic Assistants
According to a joint report from Skift Research and McKinsey, over half of travel executives are experimenting with agentic AI, even if only a few have deployed it at scale. The payoff is clear: faster service, fewer disruptions, and new operating leverage across the customer journey.
Agentic systems can now handle everything from monitoring inbound flights and weather to suggesting timely rebookings—long before a human traveler even realizes there’s an issue. Expedia’s upcoming iterations will use third-party data such as weather and local events alongside its 70 petabytes of historical travel data to create proactive, self-healing trips.
Bolda notes, “The more we start combining everything we know about you as a traveler and what’s going on in the place that you’re going to, I think it gets better and better.”
By 2026, she says travelers can “plan on it”—the era of predictive, personalized assistance will be here.
The New Travel Stack: Data as a Moat
With loyalty increasingly portable and price transparency just a swipe away, data becomes the moat. Expedia’s strategy blends three layers:
– First-party data (its massive global travel dataset)
– Zero-party data (what travelers willingly share)
– Third-party data (context like weather or global events)
Combining these fuels predictive personalization. A system can infer when a traveler is on a mission-critical trip versus a casual getaway—and tailor everything from hotel options to rebooking thresholds. The more AI correctly anticipates, the higher the emotional switching cost for consumers.
B2B as the Force Multiplier
Expedia’s B2B platform quietly powers 70,000 businesses and 160,000 travel agents globally—from banks and airlines to major retailers. It’s a model that accelerates AI learning and distribution.
Bolda has built a B2B Labs team that experiments with emerging AI models alongside partners: “We’re co-developing with our partners and figuring out the most impactful ways we can use AI to remove friction and improve traveler experiences.”
Through this lab-to-platform pipeline, innovations like Smart Trip AI move from prototype to production. Expedia’s infrastructure is also being rebuilt to be model-agnostic, ensuring partners can plug in their own assistants without constant rewrites. This makes Expedia not just a booking platform, but an AI travel operating system for others to build on.
Defining Frictionless Travel
Bolda describes frictionless travel in pragmatic terms: “Anticipating and proactively accounting for travel disruptions as they happen. Frictionless travel also means if you do need to call a service agent, they very quickly have all of the history of what’s happening in your current trip.”
That means fewer delays, fewer handoffs, and more context continuity. AI doesn’t replace empathy—it amplifies it. When an agent takes a call, they’ll see the traveler’s real-time status and suggested next steps, not a blank screen.
McKinsey’s analysis reinforces this: early adopters using AI to unify call-center data and traveler context are seeing double-digit improvements in first-call resolution and upsell rates—proof that removing friction drives loyalty and margin.
The Industry Converges on Agentic AI
The Skift–McKinsey report finds 90% of major travel companies have launched some form of generative AI project, and over half are testing agentic capabilities. What’s driving the urgency? Consumers.
In Skift’s 2025 survey, 30% of U.S. travelers said they now use AI extensively for trip planning—double the share from just one year prior. As Skift’s Seth Borko put it, “There’s a push to adopt AI, but there’s also a huge pull. Consumer behavior is already ahead of the industry.”
That’s why Bolda’s partnerships with OpenAI, Google’s Project Mariner, and Microsoft’s Copilot ecosystem are so strategic. They embed Expedia where discovery begins—inside the assistants and browsers travelers already use—bridging the gap between inspiration and transaction.
The Human Side of AI
As travel tech grows more autonomous, its most successful deployments will feel more human. The industry’s next challenge isn’t building smarter systems—it’s ensuring they serve real needs.
Bolda sums it up simply: “We are very committed to delivering more value to travelers. For us, it’s all about putting the traveler at the center.”
The Skift panel echoed that sentiment. McKinsey’s Kelly Ungerman urged travel companies to design “human-led, tech-enabled” operations—where AI automates routine tasks so employees can focus on higher-touch service. Marriott’s Drew Pinto added that AI’s biggest promise is freeing staff from repetitive workflows so they can create better guest experiences.
Skift & McKinsey See Three Arcs
Skift and McKinsey forecast the next phase in three arcs:
– 2025: Discovery gets conversational and contextual; assistants assemble day-level itineraries.
– 2026: Agents begin executing—monitoring weather, rebooking autonomously, packaging ancillaries by trip purpose.
– 2027+: Travel becomes an always-on graph of identity, inventory, and intent, unified across channels.
By then, Expedia’s Smart Trip AI and similar systems may serve as connective tissue across the ecosystem—turning every loyalty point, flight manifest, and weather alert into an input for real-time orchestration.
The Leadership Mandate
For travel brands—and any company competing on loyalty—the implications are clear:
1. Redefine AI from cost-cutting to journey design. It’s not about automating the call center; it’s about architecting anticipation.
2. Invest in data consent as a product. Zero-party signals build the trust that makes personalization possible.
3. Co-build with the ecosystem. Partner early with the assistants and platforms that travelers already trust.
Travel has always been a choreography of variables you can’t fully control. What changes now is that AI can finally act as a co-pilot—anticipating disruptions, orchestrating context, and transforming chaos into confidence.
Or as Karen Bolda told me when asked how fast this future is arriving: “You can plan on it.”