Chicago Harbors
Actually, it's usually pretty easy to get transient slips in the Chicago area (except during the 4th, the air show or Venetian Night). Belmont Harbor appears to have a lot of open slips this year, particularly on the star docks, so you might check there. 312-742-7673. Belmont is just north of downtown, and an easy walk to some of the nicest beaches and liveliest neighborhoods in the city. We winter at Winthrop Harbor (Northpoint Marina); it's a long haul down to the city -- roughly 40 miles -- and there's not much to see up there (although I agree that the harbor is nice). There's a nice little pocket-sized harbor in Wilmette, and transient space is $30/night, but it might be hard to find a transient spot for anything over 25'.