I had about ten days in Chicago, during the recent World Science Fiction Convention, at the end of August 2000.
Given that five of those days were spent in closed retreat, this is a superficial look. I had formed the opinion in previous visits (mainly on the West coast) that Americans were among the world's best and most polite drivers. I had revised that opinion by the time I had reached my hotel. Later I modified my adverse reaction. If they took the horns out of Chicago's cars, their drivers would be no worse than most. The pedestrians, on the other hand, I thought were selfish. It is all right to jaywalk when there is no traffic, but they hold traffic up.
I didn't go too far, as I was on foot. My first sortie was down to the lake (from the Hyatt Regency), and along it. I was perspiring and hot. When I turned into the city I was cooled by the wind.
The first two days (before the convention) the city was wreathed in fog.
One thing which intrigued me was the layers of road. One which went near the hotel had three levels.
This was between the Hyatt and Fairmont hotels.
I had a good view from my room. The river is crossed by 58 bridges, if I remember right. I did the boat cruise, and saw many. Here are some shots from land, though.
After the convention I went to the dinosaur exhibition, and the Pharoahs of the Sun exhibit with a friend, and the next day I went out walking the whole day.
And finally, a few more shots of buildings.