Yesterday, I spent half of my day using multiple AI tools trying to plan a short vacation for my family. I had hoped these tools could help me find the best deal that suits our current needs, rather quickly. I closed my laptop after several hours, completely frustrated.
All I learned was that we would need a bigger budget. I planned nothing, and returned to the old way of searching and planning step by step.
I love to get on the road, but, unlike many travelers, I find the planning stressful. Especially when the budget and time are tight. So I was surprised to hear Airbnb CEO Brian Chesky say that “people actually derive more pleasure in planning and anticipating travel than they do traveling.”
In a recent interview with TechCrunch, Chesky pointed out the difference between routine tasks and experiential shopping. He stressed that while travelers want an option to book flights quickly without browsing, they actually enjoy the visual process of looking at properties and exploring destinations.
“So you don’t want to take the inspiration and the browsing and the library experience of dreaming away.”
While Chesky said Airbnb will keep photos, maps and visual browsing rather than a simple chat box, he also outlined other changes.
Airbnb CEO confirms app changes are coming
Chesky shared how the company is redesigning its app experience. Rather than replacing the app with a simple text-based chatbot, Airbnb is focusing on making travel planning more collaborative and visual.
Airbnb CEO slammed chatbots usage for browsing or shopping, explaining that they only give a few options at a time and often require multiple turns.
“I think that I’ve believed for a long time that a chatbot isn’t the right interface for e-commerce. I think what you’re seeing today is also not the endgame for e-commerce or for travel or shopping,” Chesky told TechCrunch’s Ivan Mehta.
Read more: Camper company to liquidate, cancels all orders
His vision for Airbnb’s future sits between a chatbot and the original Airbnb experience.
Among major updates Chesky highlighted is making group planning easier and better.
The Airbnb CEO explained that chatbots are built for one person and that they don’t offer a collaborative interface that is important for travelers who use the platform with family and friends.
Airbnb is developing “multiplayer” features over the next three to six months that allow groups to browse, compare listings, and plan trips together in real time directly inside the app.
Seventy-six percent of group trips discussed in chat never happen, according to a 2026 Talker Research survey of 2,000 women, reported by Hotel News Resource. The survey covered only women and reflects self-reported experience, so it may not represent all travelers.
The change will try to answer the needs of those travelers who are planning a trip together with friends or family, by enabling several people to use the AI tool at once.
Airbnb is going beyond chatbots when incorporating AI into its user experience.
Airbnb wants its app to act as an agent
Airbnb is working to make its app work better with digital assistants without sacrificing the fun, visual parts of travel planning. Instead of hiding the app behind a simple text box, Airbnb wants travelers to keep using interactive features like photo libraries, interactive maps, and direct host messaging.
Explaining this balance, Chesky noted, “We want to make our app more agentic, and we want to build a lot more user interface controls.”
Chesky admitted that current automated AI assistants still struggle with real-world travel bookings. He said booking Airbnb stays through Muse and Instinct “doesn’t work very well.”
He explained that consumer AI feels clunky right now because today’s apps and AI assistants cannot easily communicate or exchange detailed booking information with each other behind the scenes.
More Travel:
- Disney World shuts down part of legendary resort
- Popular Disney World ride shut down with no explanation
- Tourists stranded as travel agency files bankruptcy, cancels trips
“I don’t think we’ve cracked consumer AI. And for consumer AI to be cracked, we have to crack at a lower substrate, and we need to make the agents [into] apps; all apps need to become agents; all must be interoperable; and all must have much richer user interfaces,” Chesky said.
For AI tools to truly transform how people shop and book trips, Chesky believes tech giants like Apple and Google would need to build a new platform for AI.
Until that big system shift happens, traditional mobile apps are here to stay, and travelers will simply see smarter, helpful AI features built directly inside the apps they already use.
“It’s really up to Apple or Google, or somebody, to build a new platform for us to really make the true shift from apps to agents,” Chesky said.
Airbnb to roll out voice tools later this year
Travelers using Airbnb will soon be able to use voice commands to search for stays and get faster help from customer support.
Amid the rising popularity of voice-focused apps like Wispr Flow, and Superwhisper, as well as built-in dictation in AI tools, Chesky agrees people will reach a point where they speak to computers more than they type.
That’s why Airbnb plans to integrate voice as a key feature of its search and customer service, targeting to roll out voice agents as soon as this fall.
Voice may be a natural next step, but travelers aren’t sold on handing more to AI yet.
Statista projects about 157 million Americans will use voice assistants in 2026, so speaking to software is hardly new.
Trust is the harder part.
Expedia Group’s April 2026 survey of 5,700 travelers found only 8% were comfortable relying on AI platforms when planning a trip. A Gartner survey from 2024 found that 64% of customers would rather companies not use AI for customer service, mostly because they fear not reaching a human.
The real test for Airbnb’s voice agents will be whether they fix problems quickly and hand off to a person when they can’t.
Related: Delta Air Lines quietly ends 17 routes while adding new flights
