Alright. Taking the kids to Chicago in 2 weeks. Best movies to show them about Chicago? They're 13 and 15 so we can do some PG-13 to soft R movies. Ferris Bueller's Day Off is on there. Thinking maybe Blues Brothers. Maybe Adventures in Babysitting and Backdraft. Any others?
Wife and I will watch About Last Night and Nothing In Common.
On a more serious note, High Fidelity.
Drinking Buddies is a dramatization of the interpersonal story behind the founders of one of our main craft brewers (Revolution). Pretty sure Joe Swanberg does a lot of Chicago-based stuff. DB's not very eventful though.
Saint Frances is Chicago though it feels more on the outskirts (Evanston). Very cute movie, but deals heavily with abortion/parenthood.
Public Enemies (haven't seen yet, and some was filmed in Wisconsin, but fits alongside The Untouchables for Chicago's history of organized crime.) Basically anything Capone/Dillinger.
Escape Room is wild. Chicago is more of a bookend setting since it all takes place inside the confines of a tower, but super entertaining. The sequel, not so much.
Inside Llewyn Davis has a good Chicago plot line, though it's primarily a NYC movie. Wish I knew more Chicago Blues/music films off the top of my head, but Blues Brothers is a no-brainer, as you've said.
Speaking of Chicago history, I've been meaning to see Judas and the Black Messiah.
Source Code is a fun "Chicago" thriller though it all takes place on an inbound Metra train haha.
Thief was pretty good too, and very Chicago in its settings.
Anyways, I love my dang chosen city and get giddy whenever it pops up as a real movie setting. Apologies for rambling.