$245 - Flights from SFO to Chicago

They’re here, finally. Flights from SFO to Chicago roundtrip for under $300. Try flying on United or American Airlines. Neither of my favorites, but heck, it’ll get me to the Windy City.

Flight Details: Any time in May, especially on United or American Airlines.

And just in time for baseball season and the end of their six months of winter. Maybe I’m a bit spoiled having lived in the Bay Area for the last four years, but regardless, spring and summer in Chicago can be perfectly temperate, and the occasional breeze coming over Lake Michigan can be welcomed during any activity.

Maybe this flight isn’t as cheap as flights to Boston, New York, or DC right now, but if you’re looking to head to the midwest, $245 isn’t bad.

Note: Flight prices to Chicago start going up in early June, going over $300 again.