I wouldn't suggest you move to Chicago. I know la few people who have moved up here from southern states and they hate it. Unless you drive (and even then), winter time will make your daily commute to work or school a bitch.

As far as driving goes, it depends on the area. Some areas are lenient, while others aren't. Generally, cops from the suburbs are assholes. They'll tow your car and arrest your ass.

School wise, I'm not sure how the whole in state tuition thing actually works but I think that you have to have graduated from a high school in Illinois to qualify.