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by RussianCow 2766 days ago
adioso.com (no longer maintained as far as I can tell, but still online) does a really great job of this, UX-wise. It lets you create searches like "departing anywhere between February 10 and March 20 for about 2 weeks", and allows you to filter destinations by continent/region, which gives you a ton of flexibility. They then allow you to choose a destination (showing what I assume is the lowest price found per destination), and then let you sort the actual flights by cheapest, fastest, and "best" (a combination of price, duration, and number of stops).

I think the computational cost is a far bigger problem for these kinds of services than the UX.