Dooner90
I rode recreationally and commuted on the South Side for many years. My advice would be to give any groups of teens a wide berth - I had a couple of near confrontations, not to mention the odd taking a swing or trying to knock me down, if I got too close. And once a group I dodged literally piled on a couple of pedestrians a moment later, beat the crap out of them and ran.
Second is, if possible, choose a route through industrial areas. No pedestrians, little traffic and empty sidewalks to ride on.