Finding the cheapest time to fly usually means checking several sites across a dozen date combinations by hand. Whentofly takes a window up to a year out plus a trip length - "5-9 days somewhere in October" - and returns the cheapest round-trips that fit, with a verdict on whether the price is actually good for that route. Free, no signup.

I've seen a lot of sites try to get this right over the years. Seems like the modern AI's natural language processing ability could be the thing that actually makes this tech work the way people think it should.

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