There are far too many to single out or list. 
http://en.wikipedia.org/wiki/List_of_people_from_Chicago
To provide a few random ones...Hillary Clinton, Ernest Hemingway, Steve Carrell, Walter Koenig, Al Capone, David Sedaris, Pat Sajak, William H. Macy, John C. Reilly, Kathy Griffin, Dan Castellaneta, Tina Fey, Walt Disney, John & Jim Belushi, Kanye West and R. Kelly (eww @ both), Michael Jordan, Mike Ditka (da coach!), and we were also a home and launching pad for Barack Obama, who spreads the word of Chicago politics (and I love it.)
http://en.wikipedia.org/wiki/List_of_people_from_Chicago
To provide a few random ones...Hillary Clinton, Ernest Hemingway, Steve Carrell, Walter Koenig, Al Capone, David Sedaris, Pat Sajak, William H. Macy, John C. Reilly, Kathy Griffin, Dan Castellaneta, Tina Fey, Walt Disney, John & Jim Belushi, Kanye West and R. Kelly (eww @ both), Michael Jordan, Mike Ditka (da coach!), and we were also a home and launching pad for Barack Obama, who spreads the word of Chicago politics (and I love it.)
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When he was jailed WsM was desparate to disown him, to no avail. We moved from there 6 years ago so I can say with relief that Archer ain't no Baron of mine any more.
Still, worth it for the comedy value alone, I suppose. 