My route proposal (239K) for the June 2005 Critical Mass ride. It’s much gayer than the other one. It also makes for a wonderful tour of pre-renewal South Side urbanism, although a truly proper tour of that would have to include much of South Shore.
Update: photos from the ride by: Art, Bob K, Bob M, Devin, Don, and Jordan. I recommend Don’s open-hydrant shots (way to avoid dousing the camera) and Devin’s shots on the Quads.