I live in Illinois and I wouldn't spend time in Chicago without an armed guard. Actually they don't observe the 2nd Amendment for citizens, preferring to let the gangbangers have all the guns. And I'd have lost my mind if you found me tooling around in my TC on Michigan Ave.
Has anyone mentioned that they sold the rights to parking meters to some sketchy outfit that jacked the rates and sent back some walking around money to the pols. Woe unto you if you get a parking ticket.
OTOH you may make it unscathed. Not likely, but stranger things have happened. If you get through OK then you should try Detroit. Now that's the big leagues.