Clever Way Round Trips

AI finds flights with weird strategies: hidden cities, nested trips, throwaway legs, and unusual routes and then returning the best unconventional itineraries.

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Inspiration

Flights from Southeast Asia to Europe are expensive, volatile, and often hard to book reliably. Many travelers, expats, and digital nomads just want a safe, affordable way home. We were inspired to use AI to uncover unconventional routing strategies that reduce cost while avoiding risky itineraries.

What it does

Clever Way Round Trips uses AI to discover obscure but practical flight strategies. It searches multi-city paths, nested round trips, positioning flights, and unusual airport combinations across SEA. The system prioritizes safe connections, lower cost, and resilient routes to help travelers get back to Europe more reliably and cheaply.

How we built it

We built the search engine using Tinyfish to orchestrate AI-driven exploration of routing strategies. The agent generates candidate flight patterns, evaluates pricing and connection safety, and iteratively refines results. A scoring layer ranks routes by cost, risk, and travel time, then surfaces the best unconventional itineraries.

Challenges we ran into

  • Airline pricing rules are inconsistent and hard to model
  • Many obscure routes look cheap but are risky or impractical
  • Handling connection safety across different airports
  • Limiting the search space while still finding creative routes
  • Avoiding strategies that could strand travelers mid-journey

Accomplishments that we're proud of

  • Found significantly cheaper SEA → Europe routes using unconventional paths
  • Built a working AI search loop powered by Tinyfish
  • Prioritized traveler safety instead of just lowest price
  • Discovered routes humans typically wouldn’t search manually
  • Created a positive “creative routing” experience instead of hacky travel tricks

What we learned

  • AI is very good at exploring weird routing combinations
  • Safety constraints are just as important as price
  • Southeast Asia has many hidden positioning flight opportunities
  • The best deals often come from multi-step strategies, not single searches
  • Constraining the AI improves real-world usability

What's next for Clever Way Round Trips

  • Add real-time price monitoring
  • Expand beyond SEA → Europe routes
  • Improve risk scoring for tight connections
  • Add “safe fallback” itineraries
  • Build a simple UI for travelers to explore creative routes
  • Personalize routes based on traveler preferences

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