Does Kayak’s ChatGPT plugin suck? Review of the best ChatGPT plugins for travel in 2023

ChatGPT’s plugin offerings can be hit and miss. I decided to explore the best ChatGPT plugins for travel so far, starting with Kayak.

Kayak’s ChatGPT plugin promises to revolutionize your travel itinerary while you work remotely. In this deep dive, I’ll explore how to book trips using Kayak’s ChatGPT travel plugin, making your travel lifestyle more accessible and personalized than ever before. Let’s dive in!

I tested the following trip ideas.

  • A work-travel hybrid trip from Houston to Bogotá, Colombia
  • A last-minute, long weekend trip from London to Vienna

ℹ️ At the time of writing (July 2023), this plugin currently resides in the ChatGPT Plus plan, costing $20 a month. Public launch dates have not been confirmed.

🇨🇴 Work-travel hybrid trip from Houston to Bogotá, Colombia

I began with a hypothetical business trip to Colombia, complete with an extra week of remote work. Starting with a deliberately vague, simple prompt, it immediately requested further details – travel dates, flight preferences, the number of people, and accommodation types – leaving me surprised with its thorough approach.

ChatGPT plugin result

It soon returned with flight and hotel options, despite my intentional vagueness. While it did make a guess at JFK as my departure city, it impressed me by suggesting three hotels right away that fit my needs.

The plugin primarily functions as a conversational guide, presenting you with basic options to explore, but doesn’t quite allow you to put a full package together. Every recommendation needs to be followed up separately, which is a little cumbersome. It’s more helpful when you’ve got specific travel plans in mind, less so if you’re just browsing for inspiration.

Pushing it further, I asked it to switch up my flight details. It did, but it overlooked my budget limit. When probed for hotel recommendations based on reviews, it fell short, sticking with previous options and introducing one new one. A cheaper flight alternative was a nice touch, showing its attentiveness to my budget concerns.

Hoping for some flexibility, I asked for direct flight options, offering date flexibility as a trade-off. Unfortunately, the plugin couldn’t handle this – a feature I’d really value and something I reckon other travelers would too.

But where it really shone was in local activity recommendations. It offered a solid list of sights and attractions in Bogota, showing a selection that could be enjoyed in a few hours. For a remote worker with limited leisure time, that’s invaluable. It was even able to provide transport options from my hypothetical hotel to these activities, complete with distance and travel times.


✨ Curious how to create a full travel itinerary with ChatGPT? Check out my in-depth guide.

To conclude, I decided to see if it could suggest local cafes with reliable Wi-Fi near my hotel. It did not disappoint, offering some excellent options with a hint of humor, and throwing in a Starbucks for those wanting something familiar.

🇦🇹 Last-minute, long weekend trip from London to Vienna

Next on my exploratory journey with the Kayak ChatGPT travel plugin, I opted to plan a last-minute long weekend trip from London to Vienna, keeping my initial prompts rather vague. I provided departure and arrival cities, alongside dates, with no further info about travel preferences or party size. Despite this, the plugin swiftly presented a couple of flight options, albeit in USD – irrelevant considering the European cities involved.

After my follow-up questions, the plugin then made recommendations in GBP – flights and hotels alike. When asked to suggest options based on reviews for a couple’s getaway, it provided a broad view, considering the location and what it inferred could be romantic, unique, or budget-friendly choices. However, it couldn’t share in-depth reviews, which means I would have to follow up on other websites – ironically, competitors such as TripAdvisor and Booking.com.

To verify the plugin’s recommendations, I clicked through the suggestions it provided. However, instead of guiding me to a specific flight, it directed me to an aggregated list of results, making it tricky to locate the exact flight I was after.

There were some cost discrepancies, and a few specific flight suggestions couldn’t be located even after extensive scrolling. Its explanation was pricing algorithm fluctuations.

I then asked for some weather-related insights and was pleasantly surprised by its considerate response, which included not just the temperatures (in Celsius, understanding I’d be coming from Europe), but also vital travel tips like power adapter information.

Next, I decided to challenge the plugin with a short itinerary prompt. It helps to be as specific as possible about your preferences (whether you love food, museums, sightseeing, prefer taxis over long walks, and so on). In my case, I kept it vague for testing purposes and asked for a ‘2.5 day’ itinerary.

The plugin won me over by smartly organizing the itinerary into morning, afternoon, and evening slots. However, it did stumble a bit as it seemed to have trouble processing the ‘2.5’ part of my request. This is something to be aware of when trying out the plugin for planning your itinerary.


✨ Interested in exploring more AI travel tools? Check out my review of Roam Around.

Pros of Kayak’s ChatGPT Plugin for travel

  • Asks up front for extensive travel details, helping travelers create better prompts along the way
  • Generates useful recommendations even when given vague prompts
  • Provides personalized flight and hotel suggestions that align with traveler needs
  • Adjusts to the user’s currency based on feedback, providing costs in GBP when asked.
  • Impressive ability to recommend local activities, including those that can be enjoyed within a certain timeframe
  • Offers transportation suggestions from chosen accommodation to local activities, including travel times and distances
  • Acknowledges when it makes mistakes and rectifies them where possible

Cons of Kayak’s ChatGPT Plugin for travel

  • Currently cannot handle flexible dates for booking flights, which could be a point of frustration for those with adaptable travel plans or looking more broadly.
  • Loading times can be slow, which might be a little off-putting
  • Tends to overlook budget limits set by the user when suggesting flight alternatives
  • Incorrectly assumes a departure city if the information is not explicitly provided
  • The plugin can’t (yet) put together a full travel package; each recommendation must be explored separately
  • Doesn’t offer detailed hotel reviews, which can be a crucial deciding factor for many travelers
  • When validating recommendations, it leads to a list of options rather than the specific suggested flight
  • Some flight prices were found to be inaccurate when checked manually

Who’s it best for?

Travelers with a clear idea or semi-formed travel plan in mind, seeking further customization and recommendations.

When to use Kayak’s website instead

Travelers who need flexibility on dates, want to take advantage of Kayak’s Best time to travel tool, or know exactly what they need and just want to go ahead and book their trip.

Kayak’s ChatGPT plugin for travel – conclusion

Overall, the Kayak ChatGPT plugin provides a smooth and intuitive user experience. It impressed me with its capabilities, intuitive error correction, and surprising depth of activity recommendations. There are a few improvements to be made, particularly around flight flexibility, but its ability to offer detailed, personalized recommendations is truly impressive.

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