Propose that we ride the perimeter of the Great Chicago Fire on Friday for Fire Prevention month (observed in October all across the nation because of the Chicago fire).  The route that comes close to the perimeter:
East on Washington from Daly Plaza
R on Wabash, L on Jackson, R on Columbus, R on Balbo, L on Michigan, R on Roosevelt, R on Jefferson, R on Taylor (after passing the origin of the fire at DeKoven), L on Canal, R on Jackson, L on Wacker, L on Orleans (Franklin Street Bridge), L on Grand, R on Milwaukee, R on Elston, R on North Ave, R on Clybourn, L on Division, L on Wells, L on Goethe, R on Sedgewick, R on Evergreen, L on N Park Ave, L on Concord, R on Sedgewick, L on Eugenie, R on St. Michael Court, R on Willow, L on Fern, R on Menomonee, L on N Lincoln Park West, R on Wiscosin, L on Clark, R on N. Lincoln Park W, R on Fullerton.  10 min break and mass up at The Nature Museum parking lot.  (end of the perimeter)
Then--North on Cannon, R on Sheridan, L on Oakdale, L Racine, R on Diversey, L on Damen, R on North Avenue.  End at Homboldt Park.

The only question I have about this route is if it is possible to get from Jackson to Orleans on Wacker (on the level that meets the bridge).