I Tried ChatGPT Plugins For Flight Booking. Here’s Why They Suck (2023)
ChatGPT plugins are now available, and it didn’t take long before big travel sites released their integrations with the AI chatbot. Companies like Kayak, Expedia, Trip.com, and JetBook.click quickly released plugins for ChatGPT 4, so I had to test them out.
After I published my article on how to book flights with Google Bard, I’ve also gotten many questions about potential Bard plugins and integrations that might come out, so I thought this was the perfect opportunity to show the potential of having these tools integrated.
In this post, I test out all ChatGPT plugins for flight booking available so far. Let’s find out if they are useful at all.
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I wrote about using ChatGPT to plan a trip and get advice when booking flights. I will use some of the prompts from those articles to make this test.
Available ChatGPT Plugins For Flight Booking
To make this test, I will use similart prompts from my previous posts on ChatGPT. My goal is not to try simple queries. Why? Simple queries are usually quick to solve directly on travel websites. Most users are able to enter the destinations and travel dates easily.
Instead, I want to discover how useful ChatGPT plugins can be in solving complex queries. These are queries with multiple restrictions, such as multiple families, traveling with pets, open jaw tickets, conditions on hotel rooms, multi-city destinations, or even budget constraints.
Then, I will compare ChatGPT’s results against how much time it takes to reach similar conclusions on my own, by just using the website. Let’s go!
1. Kayak Plugin
Kayak’s integration with ChatGPT was a no-brainer. In fact, we’ve covered Kayak before as one of the AI travel apps you could already use even before OpenAI’s big release. The new integration offers a new way of searching and booking for travel that also leverages innovative AI technology to enhance personalization and travel planning experience.

Test 1. Multiple cities, 3 flights, hotels, and car rental
My query was this.
I want to fly from Stockholm to Amsterdam on August 9th, stay downtown in Amsterdam until August 12th, then fly to New York, stay 3 nights in New York. Then, I will rent a car from New York and drive to San Francisco. Finally, I want to fly back from San Francisco to Stockholm on August 19th. Find me good flights and hotels under $150, and a good car to rent.
The results from the ChatGPT plugin were disappointing. It took about 8 minutes until it prompted an error that they couldn’t process the full question. I retried about 5 times. I only got partial results.

ChatGPT was able to digest my query into multiple ones, but the main problem was that it didn’t understand that it was a multi-city itinerary, and it searched all the flights individually (which is way more expensive)
Here are screenshots of all the individual queries ChatGPT could parse and post to Kayak.
On the other hand, my manual search took about 6 minutes. I did
- 1 multi-city city search entering the 3 cities and flight dates (for $754).
- 1 hotel search in Amsterdam, filtering under $150, and downtown (for $414).
- 1 hotel search in New York, filtering under $150 (for $429).
- 4-day car rental from New York to San Francisco (for $648).

My budget total was $2245. ChatGPT was suggesting an itinerary over $2000 just for the flights. Here are some screenshots of the options I got with Kayak.
Test 2. Best Time To Travel
Kayak recently introduced a feature called Best Time to Travel. It’s supposed to analyze historical data and use that information to guide you on when it’s more likely to get better market prices for flights and hotels (similar to Skyscanner Savings Generator, but better implemented IMHO).
My query was the following:
I want to do a 7-day trip from Stockholm to New York. When is the best time of the year to travel?
ChatGPT’s answer was again disappointing. It seems that their integration wants a date, and didn’t understand that I was trying to understand when was the best time to travel in order to get cheaper flights. ChatGPT rolled back to its general knowledge to answer.

My manual action was the following (which took less than 1 minute)
- Go to Kayak’s Best Time To Travel.
- Enter Origin, Destination, and trip length.
- Click on Search.
Then, after a few seconds, I got an answer that I should travel during October, and many other tips such as preferred dates, average hotel prices, and estimated flight prices.
Test 3. Flexible Dates
For my third test, I decided to simplify my query. Maybe I was asking for too much. So I just wanted to get information about some flights from Stockholm to Madrid, but I had flexible dates. I have the bot a few options to see what it does.
I want to travel from Stockholm to Madrid for a weekend in November 2023 (Thursday to Sunday), but I’m flexible on the dates. Find me the cheapest flights and which weekend should I go.
This time the results were actually decent. I got two options which were actually the two cheapest weekends to go to. The prices reported, however, were off. I was able to find cheaper flights after clicking on the link provided by ChatGPT.

Meanwhile, my manual search took less than 2 minutes. I went to Kayak > Flights, then I entered a date in November, added the +-3 days flexibility, and hit on search.
On my manual search, I got a matrix displayed, and I had to manually browse through the dates until I found the cheapest flights. While this view is more comprehensive than ChatGPT, and there are more options, I can understand that it can be overwhelming and confusing for some people. ChatGPT is definitely clearer and more to the point.
2. Expedia Plugin
Expedia announced their ChatGPT plugin last March 23, 2023, via Twitter. With the seamlessΒ ChatGPT Expedia integration, users can now start an open-ended conversation within the ChatGPT interface and get recommendations on travel destinations, where to stay, and even some local places to visit based on the chat.

To be fair with my comparison, I tried the same queries aw
Test 1. Multiple cities, 3 flights, hotels, and car rental
Let’s bring back the query:
I want to fly from Stockholm to Amsterdam on August 9th, stay downtown in Amsterdam until August 12th, then fly to New York, stay 3 nights in New York. Then, I will rent a car from New York and drive to San Francisco. Finally, I want to fly back from San Francisco to Stockholm on August 19th. Find me good flights and hotels under $150, and a good car to rent.
The first thing you notice is that it breaks down into multiple queries in a different way. This is a significant implementation difference, as it makes it way more interactive than Kayak’s plugin. For some people it might be better, and for others it might be boring and slow.
First, it offered me to find hotels in Amsterdam

Some of the results:
Then, searching a flight from Stockholm to Amsterdam. Here’s when things started to go wrong. This tool also didn’t attempt to search for a multi-city itinerary when it comes to the flights.

Then it tried to find a hotel in New York, and finally the car rental.
On the other hand, my manual search using Expedia took about 10 minutes and yielded the following results. Note that the interface for multi-city flight search is different and much more manual than Kayak’s. Also, when filtering out hotel prices per night you can only do it in $100 increments.
- 1 multi-city city search entering the 3 cities and flight dates (for $603).
- 1 hotel search in Amsterdam, filtering under $200, and downtown (for $599).
- 1 hotel search in New York, filtering under $200 (for $417).
- 4-day car rental from New York to San Francisco (for $288).
The grand total was $1907, whereas ChatGPT was over $3000 summing its individual recommendations.
Test 2. Best Time To Travel
The query:
I want to do a 7-day trip from Stockholm to New York. When is the best time of the year to travel?
The results were disappointing because it didn’t use the Expedia plugin at all and just fell back to the broad ChatGPT knowledge.

Test 3. Flexible Dates
Finally, the last query:
I want to travel from Stockholm to Madrid for a weekend in November 2023 (Thursday to Sunday), but I’m flexible on the dates. Find me the cheapest flights and which weekend should I go.
At first, I really got excited, as ChatGPT prompted to clarify my question. It asked if any weekend in November would work. Nice!

However, the answer was stupid. The plugin recommended flights for July! What?!

That didn’t make any sense, particularly because the tool confirmed if it was for November. Ha!
My manual search took less than 1 minute to set up, and it displayed a comparison Matrix that allowed me to search the best and cheapest dates.

3. Trip.com Plugin
The last plugin I wanted to try was Trip.com. It was released just a couple of weeks ago, and enables you to search for flights and hotels, get personalized recommendations, and even customize your itinerary in just a few clicks.

Test 1. Multiple cities, 3 flights, hotels, and car rental
The original query:
I want to fly from Stockholm to Amsterdam on August 9th, stay downtown in Amsterdam until August 12th, then fly to New York, stay 3 nights in New York. Then, I will rent a car from New York and drive to San Francisco. Finally, I want to fly back from San Francisco to Stockholm on August 19th. Find me good flights and hotels under $150, and a good car to rent.
Believe it or now, I actually liked this answer! The plugin wasn’t able to detect a multi-city itinerary, but it was still able to consolidate cheap flights. The way it displayed the results were also concrete and easy to read.
The grand total was $1976, excluding the car rental, where it suggested to check Hertz, Avis or other rentals
Test 2. Best time to travel
The original query:
I want to do a 7-day trip from Stockholm to New York. When is the best time of the year to travel?
For this particular question, the Trip.com ChatGPT plugin sucked! It started planning activities and an itinerary with things to do and links to make reservatioons on their website. Yikes. Seems that it didn’t understand the question at all.

Test 3. Flexible dates
The original query:
I want to travel from Stockholm to Madrid for a weekend in November 2023 (Thursday to Sunday), but I’m flexible on the dates. Find me the cheapest flights and which weekend should I go.
The plugin’s answers looked legit at first! But then when I expanded the options, I saw that it was recommending flights for August and July. What’s up with these tools not picking up the dates? It’s not too hard to grab the 4 weekends in November and find the cheapest flights for those.

Meanwhile, my manual search on Trip.com took 1 minute to set up, and it displayed a beautiful bar chart with all the prices for 3-day trips during November. It was very easy and intuitive to find the cheapest options using their website.

Overall, seems that Trip.com was a late player in the game and just wanted to release something to say they had a plugin available. I like the way how it presents the results in a more concrete way, but it is the most underdeveloped of all these ChatGPT plugins.
4. JetBook.click
This one I haven’t actually compared becaus the original site is in Arabic. The JetBook.click plugin is meant to help you search and book flights at the best prices, while providing multilingual information about your destination.
I’m waiting for your comments on this one, feel free to give it a shot and let me know your thoughts in the comments below!

Conclusion: Are ChatGPT Plugins Useful For Booking Flights?
It’s a good initiative, but these plugins are far from being useful yet. When they don’t crash or throw an error, they might not fully understand the queries, and usually provide wrong information or outdated results. It’s useless for budgeting purposes: all the prices I’ve seen changed when I proceeded to the booking screen.
This means that even if you use these plugins, you would still need to manually check the prices, and verify if are no better deals out there.
Ultimately, what’s the use case? On my mind, these plugins have the power to help people trying to plan a trip or arrange bookings tailor the options in a more intuitive and conversational way. For me, it’s more about complex queries, where there are lots of constraints and results that are overwhelming to navigate. That’s where most people get confused.
However, these plugins do awful in those cases. And don’t get me wrong, these websites are great! I love Kayak and have been using the since 2013 for all my bookings. But we can still do a much better job with manual searches on their websites, most of the complex queries I tried only take 1-2 minutes to input.
Another downside is that plugins are only available on the ChatGPT Plus subscription so far. Why would people pay $20 to use these plugins? The company said they will roll out plugins for free to more users later this year, but that will take time. Until today, it’s all still experimental.
I’m looking forward to the date these plugins improve (which will be in the very near future), so we can ask for the best deals on complex scenarios. Here are some of my ideas:
- I’m traveling alone with a 3-year-old kid and a small dog from Buenos Aires to Madrid next July. What’s the best airline to do that? Find me the cheapest dates to fly.
- We are a group of 5 friends that live in Madrid, Amsterdam, Stockholm, Lisbon, and Berlin. We want to hang out for a weekend in London during October 2023. We will all fly there and want to stay in a hotel close to Picadilly Circus, sharing rooms in pairs with single beds. Arrange the trip for me.
- I want to fly on a round-the-world fare with Star Alliance, visiting at least 9 cities in 45 days: New York, Amsterdam, Phuket, Bangkok, Tokyo, Sydney, Mexico, Buenos Aires, and Sao Paulo. Suggest an itinerary with the cheapest flights. The long-haul segments would be in Business Class, and all flights under 3 hours should be in Economy Class.