A different take what Chicago legends are:

• See John Hodgman's Four Dubious Fables of Chicago from the Chicago Humanities Festival. He insists that Chicago is mythical, although there may be Chicagoans...
  
• A recent Trib article pointed out some strange anachronisms on Google maps (thanks to the Map Room blog for the reference).
• Chicago Home for Incurables (thanks to the Library for the Info).  I've been on staff at UofC for almost 10 years now, and the online zoning map labeled my office, the Court Theater, the Smart Museum, and the Young Building as the Chicago Home for Incurables. For better or worse, the city's zoning map is now updated, at least for the 5500 block of South Ellis.

While we're on the subject of Chicago legends, this Sunday and next, Doc Films is screening "The Front Page" and "Scarface" (1932 version with Paul Muni). Scarface is the story of an Al Capone figure's rise and violent fall. The Front Page is based on the play by Ben Hecht, former Chicago Daily News columnist.  Check out One Thousand and One Afternoons in Chicago - a new edition published by UofC Press last year.