The only time I lived in Chicago was when I went to DePaul... it is obviously a nicer area then the south side, but there are TONS of frat boys/drunks, which is obnoxious... and there is a legitimate amount of **** walking around, holding hands and just being, well, *** as ****.
Hate me if you want, but I don't want to live around drunks pissing in alleys and homosexuals everywhere. It's cool if others can tolerate that crap, but that is part of the reason why I think the city of Chicago is for visiting, not for living in. It was fun for a few years while I could party, but I would never, ever raise a family there.
That said, I also wouldn't live on the south side. Hence, the suburbs are a happy medium.