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Remember when ChatGPT launched and every startup founder you know started throwing around the word "democratization"? Most of that was marketing fluff. But strip away the buzzwords, and AI does have one genuine superpower: it can tear through data sources faster than any human.
So I decided to turn AI loose on the often frustrating endeavor of finding flight prices that are actually affordable. Could Google’s flight tools, ChatGPT, and Claude replicate what I normally do with price comparison sites loaded on multiple tabs, all flashing warnings that there are only two seats on the plane left?
Google Flight Deals
You may have missed the news, but Google Flights got an AI glow-up and now comes with enhanced AI search through a new tool Google is calling Flight Deals.
Google says its flight tool’s main priority is helping you to save money, so until it’s time for you to book a flight, perhaps you’re better off brainstorming destinations using Gemini or one of the other top AI assistants on the market.
Once you know where you’re flying off to, visit Flight Deals and you’ll immediately notice a prompt box where all the magic will happen. The process is pretty straightforward from there. You can type something along the lines of: “Find the best round-trip air fares from LAX this January.”
However, you can also keep your options open and go down a more winding route, asking for instance, for deals to destinations that would be warm in January. Flight Deals will then focus on relevant destinations that match your description and show a more curated list of flights.
ChatGPT agent
Using ChatGPT agent to search for the best deals for round-trips starting from JFK in January 2026 saw me receive a neat table with specific dates for each destination along with the corresponding price.
ChatGPT Agent is a tool that lets the chatbot take over your actions for you, searching the web for the best current deals. You can access it by clicking the + button in the chatbox and selecting Agent.
The main disadvantage was that the flight options did not come with a direct booking link, so I had to manually search for the specified connection in a separate tab. The flight times and prices did end up matching what ChatGPT listed, so that was of course positive.
Claude
Over on Claude, things got off to a shaky start as it warned schedules for January 2026 flights “likely aren’t available yet”. Then it immediately proved itself wrong by listing flight deals for the selected month. On balance no harm done, right?
What really came in handy was Claude’s Connectors, specifically the one for travel site Kiwi. Turning on this Connector means Claude has real-time access to the best flight deals available, along with direct links to book the desired travel itinerary. In that respect, this was definitely a step up from ChatGPT.
ChatGPT and Claude research
Both ChatGPT and Claude offer deep research modes, so I asked both to look into the best strategies to land deals for flights in January.
ChatGPT consulted 18 sources and determined it’s best to book flights on a Sunday at least two months ahead of your desired departure date. It suggested avoiding rigid dates as shifting your trip by a day or two could make huge differences in price.
Meanwhile, Claude examined over 300 sources to present its suggestions. While it was a bit more thorough in its search, it also took over 8 minutes to complete the task. It corroborated most of what ChatGPT presented but did give more detailed explanations on how I could be impacted by fuel surcharges, dynamic currency conversion, and opportunities to be found in ‘mistake fares’.
Specific flights
Of course sometimes you can only work with what you have. So for my final test, I kept things very specific. I put ChatGPT, Claude, and Google Flights head-to-head, asking each to find direct flights between Chicago O’Hare and Paris for January 7-13.
My trusty price comparison website Skyscanner said such a trip would set me back around $547. So that was the price to beat.
Google Flight Deals found the same flights for $16 dollars less so things were looking promising.
Using ChatGPT without its Agent only got me indications of what kind of flights could be suitable but accurately highlighted the cheapest price I’d be paying would be around $540. Turning on ChatGPT Agent showed no meaningful improvement.
Lastly, it was Claude’s time to shine. Again with its Connectors enabled I asked Claude to crawl the internet for the best deal for my Paris trip. Within seconds it had also clocked in on the flights Skyscanner recommended and gave me a direct link showing a final price of $543.
Google Flight Deals came out on top, surfacing the cheapest option and earning a well-deserved applause. If I were to look at the bigger picture, though, the results all land within roughly the same margin of error — with prices liable to shift depending on the day (or even the hour) you happen to run the search.
Final thoughts
All things considered, you’re unlikely to uncover any special offers using ChatGPT, Google Flight Deals, or Claude that aren’t already visible on standard price-comparison sites. However, even if you’re using general AI assistants that don’t just handle flight prices, you won’t be getting ripped off.
The main upside is convenience: if you’ve started planning your dream vacation in an AI chat, you can proceed with looking for deals there, no further tabs are required.
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