I do have a car, but I plan on using the subway. Driving in Chicago sucks. I've had to do it multiple times before, and each time almost gotten into an accident, not of my fault.

Oak Park sounds nice, I'll check it out. Thanks! I've lived/stayed in New York, Tokyo, and Toronto for about a month each. So the atmosphere isn't uncomfortable to me at all. And I used to go to Chicago all the time on the train with family, but never stayed there.

All in all, I should be ok. Thanks for the tips, I really appreciate it.