I recently put a few popular AI flight finders to the test—using the same complex travel request for all of them. The goal? To find the smartest and most user-friendly AI travel tool that could handle a real-world group trip scenario.
Here was the exact prompt I used with each platform:
“Hi! Four of us are flying from different cities—Chicago, Berlin, Seoul, and Cape Town—and we want to meet in Athens. We’re flexible to depart between August 10–12, but we’d like to arrive in Athens around the same time on August 13. Please avoid budget airlines and overnight layovers. We prefer flights with good timing, short connections, and airports close to the city. Comfort matters more than the cheapest fare.”
This challenge tested a range of capabilities, including:
- Multi-city departure planning
- Flexible departure dates
- Coordinated arrival times
- Filters for airline quality and layover length
- Focus on airport convenience and comfort over price
- After trying several tools, these three stood out the most:
🥇 iMean – Best for Customized, Conversational Planning
iMean is not your typical flight search engine. It’s more like chatting with a smart assistant who actually gets what you want. Instead of checking boxes and setting filters, you just tell it your needs in natural language.
What makes iMean stand out:
- It understood my entire prompt—including the synced arrival, airline preferences, and comfort-first approach.
- Initially, it prioritized low prices. But after I said comfort mattered more, it instantly revised the results.
- It offered a personalized flight plan for each person, with coordinated arrival timing in Athens.
- Unlike traditional flight booking sites, iMean handled complex requests like excluding overnight layovers or budget airlines with ease.
This high level of interactivity is what makes iMean more advanced than any other AI flight planner I’ve tested. It feels like you’re co-creating your itinerary with someone who listens and adapts.
Perfect for: Group travel, comfort-focused flyers, multi-city coordination
Not ideal if: You want a quick booking button (iMean gives suggestions, not direct booking)
🥈 Skyscanner – Solid for Simple Searches, But Struggled with Complexity
Skyscanner is a well-known name in the travel space. It does support multi-city flight search, and its interface includes helpful filters like flight duration sliders and layover length.
But here’s the catch:
When I input all four departure cities for the same destination (Athens), it couldn’t generate results. The search would hang or return nothing, despite the tool claiming to support that kind of itinerary. That said, it’s still a great tool for individual one-way or round-trip flight planning. And its filtering system is intuitive and visual—ideal for finding shorter or more convenient flights on simple routes.
Perfect for: Solo travelers, short trips, and visually comparing flight options
Not ideal if: You need multi-person or synchronized arrival planning
🥉 Mindtrip – Great Trip Planning, Weak on Flights
Mindtrip isn’t really designed as a flight-specific AI tool. It’s more of an overall AI travel planner, with strengths in itinerary creation rather than flight discovery.
Additionally, you need to sign up to view or book anything, which slows down the process
After inputting my prompt, Mindtrip didn’t provide any flight suggestions until I asked again specifically. When it finally did, I received just one detailed flight option—from Chicago to Athens—complete with airline, timing, duration, and price. It was accurate and well-presented, but one flight isn’t enough when planning for a group of four across different continents.
Plus, you need to sign up to view or book anything, which slows things down.
Perfect for: Overall trip inspiration and itinerary ideas
Not ideal if: You need comprehensive flight search or real-time fare comparisons
Final Verdict
If you’re planning a trip with friends coming from different parts of the world, especially when timing and comfort matter, iMean is easily the best AI flight finder I’ve used. Its conversational intelligence, flexibility, and detailed custom results make it ideal for complex travel needs.
Skyscanner remains a reliable backup for simpler routes, while Mindtrip is more of a helpful sidekick when planning your entire trip, not just flights.
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