Chicago, Illinois audio tour: The Wicked City: Vice, Crime and Gangsters in Nineteenth-Century Chicago

The Wicked City: Vice, Crime and Gangsters in Nineteenth-Century Chicago

Walking Tour

75 mins

About the Tour

You may think you know Al Capone and Eliot Ness, but you don’t know the Chicagoans who came before and educated them. On this walking tour, you’ll go back in time to the city’s earliest days and hear about the first crime bosses, sex workers, card sharks, con men, saloon keepers, corrupt police officers, opium addicts, and crooked politicians.

This circular walk takes you through the River North and northern Loop neighborhoods with views of some of Chicago’s best-known public sculptures and structures. Get up close and personal with Tribune Tower, the Wrigley Building, Merchandise Mart and the city’s other top tourist attractions, as well as lesser-known ones, including:

• Brothels and bagnios
• Gambling resorts
• Cheap saloons
• Squatter settlements
• Fleabag boarding houses

There are plenty of cafes, restaurants and bars along the way for a quick or lengthy stop, including the enigmatic Billy Goat Tavern.

Why was nineteenth-century Chicago known as the “Wickedest City in the World?” Take this tour and find out!

Tour Producer


Richard Junger

Professor, urban historian and former journalist. Most recent book is "Becoming the Second City: Chicago's Mass News Media, 1833-1898" from University of Illinois Press. I'm the guy who says "guess what happened here?" as I walk around Chicago with friends.

Major Landmarks

  • DuSable Bridge

  • Chicago River

  • Franklin-Orleans Street Bridge

  • Chicago Riverwalk

  • Wrigley Building

Directions to Starting Point

CTA "L" lines -- get off at State/Lake station and walk north and east to Michigan and Wacker
CTA bus -- #19 bus runs around the Loop and stops near Michigan and Wacker and the #6 bus travels north/south on Michigan from the museums
Millennium Station -- the CTA Metra Electric lines and the Indiana South Shore Railway stop there. Just go up to street level and walk north four blocks on Michigan
Metra Ogilvie and Union stations are longer walks. Consider the "L" or a CTA bus
Parking garages -- available but pricey. It may save to use mass transit. One of the cheaper garages is under Millennium Park at 5 S. Columbus Drive. Walk north on Michigan Avenue to the bridge.

Show Directions
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Places to stop along the way

The Billy Goat Tavern is renown in Chicago legend and lore and from an old John Belushi Saturday Night Live skit. Just know your order because the cooks get testy. And remember, it's Coke or diet, no Pepsi. During the tour you can practice your cheezborger if you want to order like a local. There are many other nice restaurants along the route, including on Kinzie and Wacker. The Merchandise Mart has a larger food court and shopping on the first and second floors that are open business hours Monday through Fridays only. And there is a McDonald's at the southern terminus of the route, just about half way, if you're looking for a timely place to rest and refresh.

Best time of day

Traffic and traffic noise are worse mornings 7 to 9:30 and afternoons 4 to 6:30 local time. Traffic and noise are less of a problem on weekends. Chicago is the windy city and nearby cold Lake Michigan winds whip through the building canyons in the late fall, winter, and early spring. Check the weather forecast those times of the year.


Chicago's big buildings can do things to GPS signals. If the audio stops for an extended period of time, use the map on your smartphone to get back/stay on the route. When you move past the big buildings use the fast forward button to catch up to your location or find a spot to sit and listen to the stories you missed all at one time.
As mentioned in the tour, watch out for right turns on red lights and motorists speeding through red lights. Tour is better during daylight hours, but downtown Chicago is a safe city.


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The Wicked City: Vice, Crime and Gangsters in Nineteenth-Century Chicago