Murder, Mayhem & the Mob


Tour Number

Activity Level



City, Museums / Culture, Other


Kid Friendly: No. The subject matter is violent, vulgar, and vicious, but it can be toned down for youngsters.

Friendly: No.
You must be able to get in and out of a car.

Maximum travelers: 3



English (fluent), Spanish (basic)

Chicago's Bloody Past

Come and see the dark side of town that was once known as "The Black City. " From the legendary Levee to the infamous instruments of organized crime to the nefarious characters who gave Chicago one of its many international reputations, we'll see all the stuff you've heard about, read about and wondered about. Depending on your interests, we can cover Organized Crime, Serial Killers, or Assassinations.

This tour is also available as an all-day affair!


We will begin our journey in the downtown area, gathering the historical background for our story. We have three subject matters upon which we can focus, and we can certainly "mix and match. "

For Organzed Crime, we'll ultimately venture north to the battleground of Chicago's Beer Wars of the 1920s and more. Stops will include the Levy District, the Holy Name Cathedral, and the site of the St. Valentine's Day Massacre.

For Serial Killers, we'll meander around downtown and then up to BoysTown and Wrigleyville and then over to Wicker Park. Stops will include Death Alley, Blue Havana, and Bughouse Square.

Assassinations will take us all over the near-in area - North, South, and West - as we trace the threads of political assassinations. With just a few exceptions, every major assassination or attempt has a Chicago link.

Meeting Location + Tour Duration

Meeting location: I prefer to pick you up at your DOWNTOWN hotel, but can adjust for nearly anything.

End location: Drop-off is at your hotel or wherever you need it to be.

Duration: 2 hours

You never know about traffic, but we'll be okay!


My car comfortably seats three in addition to myself.

What’s Included

In addition to the tour, you're covered for transportation and any entry fees or parking costs we may face.

Estimated Local Cash Needed

20 USD - If we stop for a drink, you'll need a few bucks.

What’s Extra

Anything you wish to buy beyond my costs.


Though my focus is primarily with small groups, I can accommodate larger groups. If you are interested in booking for a larger group, I can meet you and guide you in your vehicle.

A Recent Review of this tour

Great tour. Clarence was very knowledgeable. The tour was just long enough.
Michael Keller

Read More Reviews For This Tour

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