While you are on the Stevenson Expressway, near Martin Luther King Jr. Memorial Drive, there is a large sign identifying the area as Bronzeville, a subsection of the Douglas Neighborhood. The area has a lot of history and, based on a little research, quite a bit of public art and historical plaques (thus, moving it up on on my list of future photo excursions).
I've never quite been able to get a photo of the whole sign because stopping your car on the expressway is very dangerous and generally frowned upon. This is the center portion of the sign. I'm pretty sure the image depicted in this logo is the Stephen Douglas statue, which is in the area.
I have a correction: The image is the Doughboy statue from a memorial, in the Bronzeville area, to 187 national guard members who died in WWI. Thanks Jim (who's informative Chicago photo blog is here)!