Legendary Chicago
By Citysearch Editors, Chicago
From former speakeasies to gangster hangouts, our editors recommend the most legendary spots in Chicago.
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Biograph Theatre
2433 N Lincoln Ave, Chicago, IL
Folklore says that John Dillinger's ghost still haunts the alley where FBI agents caught and killed the notorious bank robber. -
Site of the St. Valentine's Day Massacre
2122 N Clark St, Chicago, IL
The site where seven people where killed as part of the conflict between Al Capone and George "Bugs" Moran. -
Graceland Cemetery & Chapel
4001 N Clark St, Chicago, IL
The North Side cemetery is the resting place of Chicago's most famous citizens and political figures. -
Chess Records Studios
2120 S Michigan Ave, Chicago, IL
This landmark studio is the birthplace of most of the city's famous blues recordings. -
Green Mill Cocktail Lounge
4802 N Broadway St, Chicago, IL
One of Chicago's oldest jazz clubs (and former gangster hangout) has boasted performers like Al Jolson and Eddie Cantor. -
Congress Plaza Hotel
520 S Michigan Ave, Chicago, IL
Once known as "Home of Presidents" among Chicago hotels, its guests have included Grover Cleveland, Woodrow Wilson and FDR.
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Chicago Water Tower and Pumping Station
806 N Michigan Ave, Chicago, IL
Survivors of the Great Fire of 1871, these landmark buildings came to symbolize the city's rise from the ashes. -
Harpo Inc.
1058 W Washington Blvd, Chicago, IL
This former armory, used as a morgue after the 1915 Eastland disaster, is said to be haunted by spirits from the tragedy. -
Museum of Science and Industry
57th St and Lake Shore Dr, Chicago, IL
This Beaux-Artes style building was originally built as the Palace of Fine Arts for the World's Columbian Exposition in 1893. -
Second City
1616 N Wells St, Chicago, IL
Comedians like Bill Murray, Dan Aykroyd and Mike Myers all cut their teeth on the stage of this improv comedy club.
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Green Dolphin Street
2200 N Ashland Ave, Chicago, IL
A sprawling, high-class supper and jazz club that's risen far from its junkyard roots. -
Billy Goat Tavern
430 N Michigan Ave, Chicago, IL
This bar/lunch counter was immortalized on "SNL" for its "cheezborger, cheezborger, cheezborger."
