Hey--- I woke up in Chicago yesterday!
A close friend of mine has lived in the Ukrainian Village area for 20 years, and up until recently owned a bar in Logan Square. The Logan Sq. area is up and coming, but it can still be dangerous-- this is the big city after all. A guy was shot to death right outside of my buddy's bar this Winter--so although it's getting safer, you'll still need to keep your wits about you. Most of the violence in the city has been gang on gang--so as long as you aren't one of them, your chances of survival greatly improve.
Traffic sucks--- Rush hour starts at 2pm or so and lasts until 7pm. You will have no fun driving in the city--- although for a massive place, the drivers are pretty courteous. (well, compared to Boston at least! )
If you do take the plunge, try to find a garage / storage area for a fun car. Parking on the street, your car will die a horrible, tortured death. Between the thieves, errant snowplows, and other cars, Chicago will devour your car in short order. A low car just isn't an option in the city--- too many damaged roads, random debris, etc.
If I moved back--- I'd get a WRX /STI, and outfit it like a rally car. (higher than stock / skid plates / etc.) Then it may have a chance at surviving--- but only if you have a safe, enclosed place to park it. A good option is to buy a $1,500 beater for daily / city use, and throw it away in a couple of years---once it has started to disintegrate.
Chicago is my favorite big city-- and since Slick is from just North of the border, I'm sure he is pretty darn familiar with it. Good racetracks like Autobahn Country Club, Blackhawk Farms, and of course Road America are nearby. They have fun outdoor karts at Autobahn, and indoor karts at Chicago Indoor Karting in Addison--- which is pretty close to the city. (30 min or so)
Chicago has a lot to offer-- it would be a ton of fun to be a single 20-something in that city! At least in the Spring, Summer and Fall!