you can check out the chicago thread on here, it's got alot of good stuff on there relating to spots and such. the only shop you need to know is Uprise, off of Western and Miluakee. Wilson skatepark, off of Wilson in Lakeshore Drive is the only legimitate skatepark in the city. As far as bad neighborhoods, it's more complicated then just avoiding certain neighborhoods. If you're trying to skate, I'd suggest spending most of your time downtown, it'd eliminate your problem of venturing off accidentally into a bad neighborhood, and that's where you'd have the highest concentration of spots. But as far as sketchy neighborhoods go, you should be fine if you're not acting like an idiot or hanging around at night. good luck, PM me if you have any questions.