Some of America’s most notorious gangsters and criminals are, or were, associated with Chicago. These tours separate the fact from the fiction.
Back when the Prohibition Era (1920-1933) ushered in an organized crime spree the likes of which the United States had never seen, the undisputed kingpin of the mob was Al Capone. Using his hometown of Chicago as a base, his Chicago Outfit became legendary for its misdeeds and resilience. Indeed, chapters in the stories of many notable criminals took place in the Windy City, providing plentiful fodder for these five tour operators to offer some fantastic Chicago crime tours.
Gangsters and Ghosts 2-Hour Walking Tour
If you believe in ghosts then you can bet there are plenty of them roving around Chicago as a result of the underground crime world. This fun walking tour blends hearsay with history to paint the picture of a city with a dark side. Visit the Chicago Loop, where speakeasies thrived during the Prohibition years, as well as the places frequented by Al Capone and his cohort. This great alternative city tour usually runs around four times a day over the morning, afternoon and at night. From $35 per person.
Untouchable Tours Chicago’s Original Gangster Tour
Donning the garb of a gangster is a pretty common fancy dress party theme, so it makes sense that your Chicago crime tour guide would do the same. This is a lively tour that explores the history of Chicago. In this case, the itinerary is all about the notorious Prohibition sites, such as the place John Dillinger was killed, and where the St. Valentine’s Day Massacre took place. Transportation between the sites is provided and this tour runs Fri-Sun only. From $45 per person.
Chicago Mob and Crime Bus Tour
Hop aboard the big red crime bus to be transported to the Windy City’s underworld. This 90-minute tour visits key crime locations around the city, such as Chicago Criminal Courthouse, and then traces the steps of various criminal enterprises to learn how their members ended up there, if not six feet under. Other well-known crime scenes are visited along the way, including Holy Name Cathedral and Biograph Theatre, each one tied to the mob by gripping stories of greed and corruption. From $46 per person.
Chicago Crimes Night Tour
Nothing adds a frisson of excitement to a crime tour like doing one at night. Luckily, this tour takes place by bus, so that you can get comfortably between the landmarks made famous for infamous reasons. Walk in the final footsteps of Hymie Weiss and John Dillinger, among other notorious murder sites, experience the Loop, River North, Lincoln Park and other neighborhoods with a past, and hear the stories of Al Capone and many other mobsters along the way. This tour runs Mon-Fri from June-Oct, and Mon, Thu and Fri for the rest of the year. From $52 per person.
Chicago Gangsters and Food Tasting Walking Tour
It really does speak of the state of the modern world where eating while discussing grizzly crimes is a thing. And yet, we must also remember that Chicago is also famous for, among other things, its delicious deep dish pizza. Learn about the exploits of Al Capone, and wander through secret tunnels he and his cronies used in the past for bootlegging booze, then take an incongruous sidestep to a restaurant, for tastings of the two Chicago styles of pizza: deep dish and the older tavern style. From $75 per person.