My family have a few favorite Chicago landmarks.
First, the Buckingham Fountain --- looks great in a summer evening. Since parking is terrible downtown especially by the fountain, there was one time were my husband had to wait in the car (double parked) while the kids & I checked it out.
Second, the Wrigleyville --- great concert location. We saw The Police Reunion (Sting) here last year and it was fantastic!
Lastly, the Sears Tower. My husband used to work here, so when we go to the city and you can see the tower, my son begins to say who was 6 yrs. old then now 8 --- "look! there's papa's work ... the Serious Tower".