Yeah I've noticed a lot of them from the train too, but they definitely sketch me out haha. I know of a bunch of abandon places on the west side, but I'm trying to avoid that city because I used to cop out there for years, plus cops fuck with me constantly because I'm white and in general it's just not a place I would want to live, but unfortunately it's the only part of the city I'm familiar with 100%. As you can see I'm in a pretty big pickle but I definitely appreciate the feedback. But as you suggested, I'm going to just take my chances with talking to strangers considering I have nothing to loseThere are tons of abandoned buildings in Chicago though. I don't know much about squatting or specific places really, but it doesn't seem like it would be too hard in a city like this. I see a lot of abandoned industrial-looking buildings along the metra tracks coming down from the northern suburbs. Those are probably shitty places though because they're right a long the tracks so you'll probably be seen pretty easily and also I have no idea what kind of [potentially hazardous] stuff used to be made/was used in those buildings so I dunno, I personally would avoid them. Like I said I don't really know much about squatting, but I'm just throwing out ideas.
Sometimes when I'm in
HipstervilleWicker Park there are some Crusty Oogle types hanging around so you might be able to talk to those guys/girls and get some info?