Skift Take

The industry is getting closer to the vision of the comprehensive digital travel agent, but it's still far away.

Despegar and Kayak both released travel planning and booking tools this week meant to integrate generative AI more comprehensively., Expedia, and several other big companies released simple chatbots powered by ChatGPT about a year ago. Those chatbots have generally existed as independent interfaces, doing little to really transform the travel planning and booking experiences as industry experts have touted.

While the business models for Despegar and Kayak are different, the new tools give us a better understanding of how the future could look. 

Despegar is an online travel agency primarily for the Latin American market. 

Kayak is a metasearch site owned by Booking Holdings, meaning it compiles options from various booking sites, allowing users to compare rates and navigate to a third-party site for bookings.

Gonzalo Estebarena, the chief technology officer of Despegar, said the new tool is the first version of what he believes will be the future of how the Despegar website operates. He sees the tool evolving as a virtual travel agent that will be able to accompany the guest before, during, and after a trip.  

“I think that eventually, this will completely replace not only our website, but I think this type of logic … will be the next wave of web or app design,” Estebarena said.

The days are still early for generative AI, so the technology in the beta version of these tools is limited. While there aren’t as many errors in the results as AI chatbots from last year, there are enough bugs that today’s users will likely return frustratedly to the Google search bar. 

See some quick tests below on how each of these platforms perform — the good and the bad. 


The tool at Despegar is called Sofia. It’s built in Spanish to accommodate its main clientele. 

The interface includes a chatbot panel on the left side of the screen, which is supposed to connect to the main portion of the screen. 

The user can either ask the chatbot a question or select one of the suggested prompts on the right.  

For now, the tool can share information about a destination as well as flight options. The company plans to integrate all of its products into the tool next — including hotels, activities, and car rentals — followed by connections to third-party products like Uber. 

Some other issues:

  • The chatbot said it would converse in English, but it reverted to Spanish when encountering an issue. 
  • The chatbot and the main screen often don’t connect as they are supposed to.
  • The chatbot can get “stuck” if asked too many questions in the same conversation, so the user would need to start over.  


Kayak’s new trip planner is called Ask Kayak.

Users can start by asking a variety of questions about a specific destination or a suggestion about where to visit. 

When it comes time to purchase a flight or stay, Kayak links the user to the relevant online travel agency for booking. 

Kayak did a good job of showing flight, lodging, and car rental options for a certain destination, along with other helpful features like tools showing the best times to fly and relevant destination info.  

It did not do well connecting those options in response to a prompt about cultural events in the next several months. It only showed general information about destinations and their events. Ideally, it would show specific information about when those events would occur and then show flight and hotel information based on those dates. 

The chatbot portion of the tool is powered by ChatGPT and is “presented as-is and without verification” by Kayak, according to the website, meaning it is likely limited in its ability to scout the internet for up-to-date information on certain topics. 

Some other issues:

  • The response to a question about upcoming cultural events in Berlin gave results for multiple German cities, Berlin included. 
  • This chatbot can also get “stuck” if asked too many questions in the same conversation.
  • Clicking on a button to view hotel options opened a page that showed flight options. The hotel options were in a different tab of the page that opened.

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Tags: artificial intelligence, chatgpt, despegar, generative ai, kayak, online travel newsletter, trip planning

Photo credit: Despegar and Kayak each released new AI trip planners. Pixabay

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