The times I've been in Chicago, I've parked my car in the hotel lot and walked wherever I needed to go. The first time I was there, I noticed that every last Chicago PD car I saw had body damage, and I figured if the freaking cops were getting hit, I didn't want any part of driving in that town.
Yeah, I've only been to Chicago proper 1 time YEARS ago and I was a passenger the whole time. Of course, the whole time I was also reminded why you don't let Texans drive in the snow. I swear I thought my boss was out to kill me and everyone around him.