This photo is from a while ago (you can see the snow, and even in Chicago it doesn't snow in May) but it is nicely illustrative of the topic at hand.
The topic at hand, is, TRAFFIC.
Today it was raining. Walking back with a friend who didn't have a coat, so we took a cab, and it was TEN DOLLARS to travel about 8 tenths of a mile.
Chicago traffic is just nuts, especially after the Dan Ryan construction has begun. It is literally impossible to move about most days.
The Chicago metropolitan area is in fact bigger than a commute radius. If you live out past Aurora, for example, it isn't really feasible to commute to a far suburb in a day, unless you want to spend 1 1/2 to 2 hours in your car each way. That level of commute is beyond the pale for most people.
My advice to anyone new to the city is to move on a METRA train line if you are in the suburbs, or move near an "L" train line if you are in the city. The bus, in most circumstances, can't be relied upon. The "L", however, is pretty good, but there are few "express" trains so it is a pretty hard slog to get to and from work that way. The METRA, on the other hand, which is commuter rail, works pretty well in all directions and has multiple "express" trains that really cut the time down to something managable.
My final comment on traffic is what a friend said to me years ago. He said his father sat next to someone who would start every day with a long, drawn out discussion of traffic. One day his father stood up and said:
"There is NOTHING more boring than hearing about your commute!"