Sorry but nothing is on the Chicago scale of stupid but Chicago.
Coming into town a couple of years ago on I-290. Traffic was crawling. After about half an hour we came to the cause - a car stalled in one of the center lanes. Two little kids in back smiling and flipping the bird at every car that passed them. Gotta love the Windy City.
When I made pickups in Michigan that were headed west I would go up and over into Wisconsin whenever I could rather than deal with Chicago.
The best thing about Chicago?
Seeing it disappear in your mirrors.