It’s hard to believe, but we’re only a few weeks away from Halloween, and after that comes November—and the unofficial start of the holiday season. If you travel during this time, you’ll know that finding cheap flights can be difficult. To get the best prices, people traditionally turn to comparison sites like Kayak and SkyScanner.
However, as artificial intelligence seems to be taking over everything, and the tech industry won’t stop shouting about its benefits, I decided to try three conversational AI tools to see if they could help me find the cheapest flight deal for the Thanksgiving period. Here’s how that went.
Flights listed on ChatGPT
The first tool I turned to was AI chatbot king, ChatGPT. I gave it the following prompt for a hypothetical holiday trip, which is the exact same prompt I issued the other AI chatbots I tried for this article: “I want you to find me the cheapest tickets for a round-trip flight for this Thanksgiving period. My departure city is New York City, and my destination city is Dallas.”
ChatGPT asked me a series of questions about trip specifics, including exact dates and preferred airports, or gave me the option for defaults it selected (all NYC → DFW/DAL airports from Wednesday, November 26, 2025 to Sunday, November 30, 2025). I chose the latter.
OpenAI’s chatbot then spit out a bunch of information, including which airlines and airports had the cheapest options, and asked me if I wanted to see further results on specific itineraries. It even offered to show me total landed cost options (which means it would let me know how much the flight would cost if I checked bags, too). It also offered to set up price alerts for me.
But it didn’t stop there. As ChatGPT will carry on a conversation for as long as you want (and as I didn’t want to ask and answer questions for 30 minutes), the chatbot also gave me three “ABC” options:
- A — Show me the three absolute cheapest round-trip itineraries (all carriers, show baggage fees).
- B — Show me the three best nonstop options (if any) ranked by total cost & convenience.
- C — Compare a cheap Spirit/Frontier itinerary versus a reliable nonstop (AA/Delta) including checked-bag costs. [ChatGPT previously told me low cost carriers often show the lowest base fares].
I chose option “A”. Ultimately, ChatGPT returned three itinerary options with the absolute cheapest with one checked bag being between $190 and $220. It also gave me a direct link to the carrier’s website so I could book that option.
Flights listed on Google Flight Deals
Now that I had ChatGPT’s answer, I next gave the same prompt to Google’s new Flight Deals, its AI-powered Google Flights search tool. Google launched Flight Deals last month, billing it as an “AI-powered search tool within Google Flights” that “is designed for flexible travelers whose number one goal is saving money on their next trip.”
Flight Deals lets you prompt the service like you would “as though you’re talking to a friend”—in natural language—and it will return flight itineraries that best fit your needs.
I entered the same prompt I used with ChatGPT. Frustratingly, Flight Deals then asked me to confirm where I was flying from. I replied with “NYC” and then had to also select “New York” from the drop-down menu.
However, I only received one result: a $249 nonstop United flight from Monday, November 24, to Friday, November 28. Flight Deals said it checked departures between Nov 24 and Nov 27, and returns between November 28 and December 1, which generally matches the “Thanksgiving period” I indicated in my prompt.
A disclaimer for the results stated that “The results shown are flights that are either significantly cheaper than usual for a route, time of year, trip length, and seating class, or are among the lowest-priced options for destinations that match your search.”
Unlike ChatGPT, Google Flight Deals did not allow me to ask follow-up questions or provide any tips on finding cheap flights. It also didn’t tell me whether the $249 flight included checked baggage. Clicking on the sole result took me to Google Flights’ traditional interface, which showed additional flight results.
Flights listed on iMean.ai
Finally, I gave the same prompt I used for the others to iMean.ai, one of a growing number of dedicated conversational AI travel assistants.
Even though iMean.ai’s interface looks like a more colorful version of ChatGPT, the site’s AI agent didn’t waste time asking me questions in an attempt to refine my prompt like OpenAI’s chatbot did.
Instead, it informed me that it searched through 302 flight options and determined that the best itinerary matching my query was one that split the departure and return flights between two airlines. The outbound flight leaves New York City on Wednesday, November 26, and the return flight leaves Dallas on Sunday, November 30. The total cost: $334.
iMean.ai’s agent, like ChatGPT, provided me with the option to continue chatting with it to ask more questions or refine my needs. And unlike ChatGPT, iMean.ai displayed the results in a useful split-screen interface that helpfully laid out details, such as flight times, for each leg of the trip. Clicking on the accompanying “View” button took me to Kayak, where I could buy the selected tickets.
Should you use AI chatbots to find cheap flights?
In the end, consulting with three different AI tools resulted in the agents returning three different flight options for my hypothetical Thanksgiving trip, all on different dates, different airlines, and at different price points (ChatGPT: $190 to $220, Google Flight Deals: $249, iMean.ai: $334).
Based on price alone, ChatGPT found me the cheapest tickets for a flight from New York City to Dallas during the Thanksgiving period. But though I was happy with the price, the experience of using AI chatbots to help me find cheap flight deals left me with a nagging feeling: uncertainty.
ChatGPT presented me with too many questions and options. I felt that if I kept engaging with it, I would be sucked into a never-ending succession of possibilities that would make it nearly impossible to choose. When was the right time to stop prompting and make a choice? I didn’t know.
Conversely, Google Flight Deals provided me with a single option. This left me unsure as to whether it was actually the best choice (according to ChatGPT, no).
iMean.ai was a mix of the two. It was conversational like ChatGPT, but provided fewer options, like Google Flights. However, it also presented me with an option that was more expensive than the ones both ChatGPT and Google Flight Deals presented, leaving me questioning its results.
Ultimately, my experience with the three chatbots left me wanting to return to the traditional flight comparison websites, like Skyscanner and Kayak, that I am used to.
If you’re thinking of using chatbots to find deals on flights for this upcoming holiday season, it can’t hurt to check out various AI agents to see what information they return, but I’d still check the results of any AI recommendations against the results of traditional flight checking tools.