I've always lived with friends/roommates and am now currently living with my girlfriend, which is a 2 bedroom for $975 (basically a STEAL in a nice northern Chicago neighborhood). Have you thought about looking on criagslist for roomies? That's how I found 2 guys I lived with for about 9 months and lucked out that they weren't weirdos, were my own age, and we got along pretty well.
Holy fuck what neighborhood is this? I'm in Lincoln Park and my 3 bedroom place is $2100 which relative to my friends' places is a steal.