The CTA 2011 calendar mostly focuses on transit shots, but there are some good streetscape shots as well.
http://www.transitchicago.com/assets...l_Calendar.pdf
The January photo is of the Halsted, Blue Island, and Harrison 5-way intersection, formerly a pretty major neighborhood nexus. Everything in the photo is gone, demolished in the late 1950s and early 1960s for expressway construction and the new UIC campus.