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Re:Ask HN: What interesting problems are you working on? by nwsm on Tuesday January 28, 2020 @08:36PM (#22176288)
That really is a hard problem. Here is a very good slide deck [0] detailing the complexity of flight search. It's written by an employee of ITA Software, who built QPX, the system that was bought by Google and now powers Google Flights. [1]

[0] http://www.ai.mit.edu/courses/6.034f/psets/ps1/airtravel.pdf

[1] https://en.wikipedia.org/wiki/ITA_Software

Re:Ask HN: What interesting problems are you working on? by beatthatflight on Tuesday January 28, 2020 @08:52PM (#22176393)
Haha, I very nearly quoted that deck in my summary, I've read it a few times. When people ask "why can't you just show the cheapest flights" I usually pull out their Chicago example. The computational complexity is just enormous.

I've found, however that for one way routes I can do fairly well, and for return journeys I have to just sample the space and hope that I'm hitting some good dates in there, currently.