The Hidden Hurdle in AI Travel Planning: Chatbots That Ignore the App – Skift

Welcome to the forefront of conversational AI as we explore the fascinating world of AI chatbots in our dedicated blog series. Discover the latest advancements, applications, and strategies that propel the evolution of chatbot technology. From enhancing customer interactions to streamlining business processes, these articles delve into the innovative ways artificial intelligence is shaping the landscape of automated conversational agents. Whether you’re a business owner, developer, or simply intrigued by the future of interactive technology, join us on this journey to unravel the transformative power and endless possibilities of AI chatbots.
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Photo Credit: The Expedia ChatGPT app in the directory.  Screencaptured/Skift
Travel apps inside AI chatbots are starting to look like real referral channels. The catch, Skift’s testing found: A brand can be connected and still get skipped.
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Travel apps inside AI chatbots can now return branded results, prices, and booking buttons. But Skift tests found a catch: The user needs to connect the app and the chatbot has to know it’s available and choose to use it.
That first step is a big hurdle for everyday users who aren’t familiar with the apps. The second step is where the referral path can break.
In Skift’s tests, Claude — which calls these integrations ‘connectors’ — handled them better than ChatGPT. It surfaced and used travel apps with little friction, while ChatGPT repeatedly bypassed or denied those that were already connected.
Several major travel companies have rushed to add apps to the AI platforms. 
We looked at Booking.com, Expedia, and Viator, and even when we’d connected them inside ChatGPT, the bot initially said it could not use them. In each case, the app eventually worked — but only after added prompting. The results reflect just a snapshot of w
Curated by Dennis Schaal
Executive Editor
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Tags: artificial intelligence, booking.com, chatgpt, Claude.ai, expedia, the prompt, travel technology
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Skift tested how travel apps (“apps” in ChatGPT, “connectors” in Claude) actually perform inside AI chatbots and found a widening gap between availability and usability. While branded travel integrations from Booking.com, Expedia, and Viator can return live listings, real pricing, and deep-linked booking buttons, getting the chatbot to actually use them is inconsistent. ChatGPT repeatedly bypassed or denied connected, authenticated apps—offering elaborate but false technical excuses—until users pushed back forcefully (even typing “You are wrong”). Claude, by contrast, proactively surfaced relevant connectors in context, letting users activate and use them with little friction. Expedia confirmed the ChatGPT behavior is a known platform bug. Because chatbot answers increasingly shape which brands travelers reach first, this in-chat surfacing has become a new layer of referral risk: being available in an AI chat is not the same as being surfaced by one. The commercial model remains unsettled, with OpenAI also running ads (Booking and Expedia ads appeared under rival results) while Anthropic pledges to stay ad-free.
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