600 North Clark Street
Tours depart Mon-Wed 10:00; Thurs 10:00, 13:00; Fri 10:00, 13:00, 16:30; Sat 10:00, 13:00, 17:00; Sun 10:00, 13:00
The days of Al Capone are long gone, but Chicago's notorious past is still good for business, it seems, given the popularity of these "Gangster Tours." The 2-hour bus trip takes you to all of the city's old hoodlum hangouts from the Prohibition era, including O'Bannion's flower shop, the site of the St. Valentine's Day massacre. The focus is definitely more on entertainment than history (guides with names such as "Al Dente" and "Ice Pick" appear in costume and role-play their way through the tour), but the trip does give you a pretty thorough overview of the city.
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