drunk on the train to Chicago, I feel alright

I'm seriously considering moving to Chicago at the end of the year (with the understanding that winter is a terrible time to move anywhere) - my lease will be up, I've sworn to quit my job come November, and I need to get the hell out of Texas. Chicago seems a good fit for needs both practical (a large city, not too expensive, with a good public transit system) and sentimental (I was born in Aurora, IL).

So, anyone here from Chicago? And willing to let me pick your brain? I have questions and a lack of contacts in the area.