Chicago is such a great city to walk around. A transit pass is cheap and will get you everywhere fast either on the subway or the "L".
The old water tower and Museum of Contemporary Art are close together
Navy Pier is a must see
While at Navy Pier take the Sea Dog 75-minute River and Lake Architectural Tour, this was too much fun but be sure to make reservations
The lions outside the Art Institute are famous
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The Picasso sculpture was quite controversial when it arrived in 1967
I have photos of my Mom at Buckingham Fountain, built in 1927 it is a Chicago landmark
Chicago is full of public art like The Four Seasons by Marc Chagall
The Willis Tower (it is really the Sears Tower) at the time of its completion in 1973, it was the tallest building in the world. The observation deck has a 360 degree view of the city (on a clear day) but if you can't see the top from the street because of clouds don't bother.
There is much more to discover, you are going to have a blast.
Wayne