I've always hated how everyone says flat out, "avoid the south and west side, if you know what's good for you." The south side is just boring, but definitely has some sketchy areas. The west side, however, is fucking great and you'll find the best food in the city out there. Obviously, both sides have streets you do NOT go down if you're a preppy white boy, but the same can be said for any city. Also, the north side has its fair share of dangerous neighborhoods (hi, Rogers Park). I know way, way too many people who have moved to Chicago, live in the safe neighborhoods, and then proceed to loudly exclaim, "I don't know why everyone says Chicago isn't safe, nothing ever happens to me!"
I fucking miss Chicago, but I can't ever live there again.
PS, would anyone be willing to buy me a Pequod's pie and ship it to NY? That'd be rad as balls. I miss deep dish pizza so, so, so much. The only deep dish in NYC is Uno's, and it's not even real Uno's pizza!