Great shot. I like how his outfit is almost like a camouflaged compared to the color of the wall behind him. I also like you composed the image to have your subject fall in the rule of thirds, and I think the brown paper bag in the gutter adds to the scene. Lots of nice vertical lines contrasted with the long sweeping horizontal line of sidewalk curb.
I live in the Chicago area as well and I like this shot. Is that the beginning of the overpass on the upper right? (the el?). This certainly has that "Broadway" look to it. One thing for sure, the Broadway in Chicago is very different than the Broadway in NY.
