I think this was discussed on the Podcast a few weeks ago but I’m interested to hear what others have to say.
Unfortunately for me the most recent and biggest budget depiction of Chicago is in Watch Dogs. While that games sins have been picked apart many times what annoys me the most is that there were clearly people on staff that knew the city very well. Every once and while there would be an intersection or L station that was very accurately detailed. The Soundtrack had great local bands like The Lawrence Arm or J.C. Brooks and the Uptown Sound on it. The weirdest detail the got right was the boat yards. Since the lake freezes over they have to move all the boats out of the marinas. So in industrial parts of the city they have yards with boats wrapped in tarps stacked in columns of three or fours on scaffolds. It such a bizarrely specific detail to get right in a game that put a goddamn mountain in the suburbs.