Here's a 16mm gem from the Chicago Film Archives: an hour-long look at Chicago between 1941 and 1960, shot over a 19-year-span by the late Chicago amateur filmmaker and attorney Marion Kudlick.
It's a pretty easy hour to watch, especially when you see 1940s Chicago—normally seen these days in black and white—in color. North Michigan Avenue makes an early appearance and the Historic Water Tower and Pumping Station were still tall enough then to dominate the view.
Michigan Avenue looking south from near Adams pops up at the video's 2:30 mark. The streetwall is virtually unchanged since then.
And in a shot that looks from the roof or upper floors of the Congress Hotel looking east, we get a rare color look at intersection of Congress and Michigan before it was widened to accommodate car traffic headed to (and from) the Eisenhower Expressway. You'll see it was a beautiful pedestrian plaza with a gentle rise of steps leading to the bronze Bowman and the Spearman sculptures. Too bad it was all ripped up in the name of progress.
Kudlick also takes his camera to the neighborhoods and suburbs.