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Sounds like a P/NP-type problem. It's quite a hard problem to calculate all possible permutations of routings and schedules across 5 cities ("NP"), and United's system clearly isn't up to snuff for it, while Google's is.

But validating and pricing any single itinerary is a trivially easy problem ("P"), so United can handle that no problem. It can't come up with the itinerary, but given a particular one, it will sell it to you.

On multi-city trips, usually the UI allows the user to select each leg individually, so it is a very trivial problem (i.e., the same as 5 one way trips).

So no, there's no special magic here.

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