I live just south of Chicago and should visit more. Be careful, tourist areas are as safe as anywhere but a lot of very dodgy parts of town, mostly on the South and West sides. Wrigley Field is worth a visit (Cubs baseball) with great bars all around including a Scottish bar I think called The Duke of Perth. The Rush/Division area on weekends is like Benidorm or something with lots of drunken women and bars open till about 4 or 5, worth seeing but with your girlfriend you may not quite enjoy it as much. Bears football tickets can be tough to buy but on the day you may get lucky and not ripped off too much if you buy outside from scalpers (touts). Taxis are everywhere but few drivers speak English and public transport is very good. If you get a chance I think the best music bar in America is The Hideout Bar, affiliated with Bloodshot Records and great live music. Its a bit off the beaten track though.