Skift Take

None of the AI tools are as sharp as users may expect — but the companies that have begun experimenting likely are farther ahead than those that have not started at all. 

Many of the travel booking platforms that experimented with generative AI tools early are now releasing second or third versions of that tech. 

That’s been the case for Expedia, Kayak, and HomeToGo, all of which have announced upgrades or new AI tools in recent months.

Based on the tests that Skift has been able to do so far, none of the tools are as sharp as users would like — but those companies likely are farther ahead than those that have not started at all. 

Some of the projects highlighted below will be part of the discussion next week at the Skift Data + AI Summit in New York City. Kayak chief scientist Matthias Keller and Expedia chief architect Rajesh Naidu are slated to speak, among others.


Expedia earlier this month said that it would be adding multiple AI tools for various parts of a trip, including inspiration, planning, booking, customer service, and more. 

The main tool is Romie, an AI-powered travel agent and assistant. Users can access the chatbot individually or in groups on Whatsapp, text message, or the Expedia app.

A quick test in WhatsApp shows that Romie can answer questions about destinations and provide options with links for flights, hotels, and activities. Clicking on a link opens that product in the Expedia app. 

(Expect a full test soon detailing how these multiple features work.)

Romie is able to proactively suggest alternatives if there is an unexpected event that could cause a travel disruption, like poor weather or a flight delay, according to the app.

The Expedia app is also getting an itinerary builder and a tool for users to compare destinations. The online customer help center has been updated with AI to resolve problems more quickly, the company said, and guests can now view AI-generated review summaries for at the top of each individual hotel’s review page.


HomeToGo, the Germany-based booking site for vacation rentals, last week shared its vision for an AI assistant that helps users with search, booking, and post-booking support. 

Completion of a “Super AI Sunny” chatbot is the goal, but the company is building it in steps.  

HomeToGo is testing one of those building blocks in a new customer service chatbot called AI Sunny, which repurposed the previous traditional chatbot. The company said that so far, AI Sunny has reduced the transfer of customers to human agents by about 40%. 

AI Sunny is in addition to an AI-powered search tool, called AI Mode, which Skift tested after it was released last year.  

HomeToGo plans to eventually merge the AI Sunny and AI Mode products to create the foundation of Super AI Sunny for three uses:

  • Enabling guests to search for a rental using everyday language. For example: “A two-bedroom villa with a pool that’s close to great hiking trails in Italy.”
  • Answering questions about specific rentals on topics like cancellation policies and parking options
  • Providing tips based on the rental location, such as packing lists, local restaurant recommendations, and weather forecasts.

HomeToGo also said last week that it’s using Google Cloud’s Vertex AI to build various products as part of a goal toward a reimagined marketplace fully powered by AI. Vertex AI gives software developers access to several third-party generative AI models in addition to Google’s, allowing the developers to select which model is best suited for each individual project. 

Google’s Gemini model powers HomeToGo Smart AI Reviews, a tool in testing that summarizes a property’s guest reviews and highlights key features.  


Travel metasearch engine Kayak earlier this year released the first version of a reimagined travel planning and booking process, a tool called Ask Kayak.

The user starts with a prompt in everyday language about a specific destination. The tool then opens a full webpage with options for flights, lodging, and car rentals, along with AI-generated information about the destination.  

As the Skift test from March showed, the tech still needs some work  — but CEO Steve Hafner is hopeful that AI will lead to a better future for online travel booking companies. 

Kayak was one of the first travel companies to announce a plugin on ChatGPT Plus. It allows ChatGPT to provide information and links about specific flights based on information from Kayak.

Along with Ask Kayak, the company released a tool meant to read flight fare information from a screenshot and then search for a better price. 

Kayak is owned by Booking Holdings.

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Tags: artificial intelligence, booking holdings, expedia, generative ai, hometogo, kayak, online travel newsletter, the prompt, very online

Photo credit: HomeToGo shared its long-term vision for an AI-integrated marketplace. HomeToGo

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