I'm afraid I don't know Chicago at all. But I have been in your position.
I'd just like to suggest that you can make it. Keep to your principals, don't impose them on anyone else, (you can never sort out the world anyway), and watch for opportunities. Try to keep clean.
Watch your stuff and don't collect too much. Keep your cash in your pocket.
At the risk of sounding overbearing, stay away form all intoxicants. You need a clear head. Not to mention the money.
Believe me, you will make it.