Along the Dan Ryan Expressway there are medallions with six different designs on them. I was able to get pictures of four of the designs as we rode by recently.
Searching the internet, I finally hit on the right combination of search terms that led me to figure out what they were. The Dan Ryan Art Wall Project was part of the Dan Ryan Reconstruction work in 2006-2007. There are 146 of these medallions with six designs. Two of the designs below, the city scenes, were designed by Chicago Public Schools students with guidance from a Chicago artist (Bernard Williams who designed the other two medallions below) and the Little Black Pearl Art Center. I missed one of the CPS Design winners and the IDOT logo.