Private tour in Chicago Bob K

Chicago Gangster Tour

4.3

(3) reviews

-
Hours icon 3 hours
Private transportation
Private tour for 1-3 people
Your party size

1

Tour date
View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later
-
Hours icon 3 hours
Private transportation
Private tour for 1-3 people
Your party size

1

View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later

Bob K.

5.0

Guide rating

107

Reviews

Tours delivered

3 hrs

Avg. response time

The Experience Create your own memories, giving you a front row seat, Making you the Star in your own movie! Hello my name is Bob , a life long adventurer & avid traveler. I will make your time in Chicago a very special time to treasure. Born & raised in the City, I know that I can open doors to a one of a kind memorable experience. I am an Artist having traveled all over the U. S. doing Art Fairs & internationally as Artist for Club Med. I have an intimate vision & understanding of what visiting & touring a new place is all about. I was artist for the State of Illinois. Artist in residence for the development of the Museum Campus. I have a Master's in Historic Preservation from the Art Institute of Chicago. After 20 years, I recently retired from the City of Chicago as Director of Community Outreach. My intimate knowledge of the inner workings of the city allow me to offer a total immersive experience, not available on other tours. From wherever you come from, I will make you feel comfortable, safe and at home. I was artist for the State of Illinois for the turn of the Century I was Artist in Residence for the development of the Museum Campus I recently retired from the City of Chicago , after 20 years as Director of Community Outreach Worked closely with the mayor's wife, Maggie Daley on art projects for Youth throughout the city. I am considered a great raconteur & storyteller. Some tours will use transportation either Uber or I will get a car.

Have a question or want to customize this tour? Message Bob K.

Overview of your Chicago tour

My tour of Chicago mobsters will focus on the Prohibition Area starting in the 1920's, Continuing til the beginning of World War ll. The other half of the tour will focus on the post World War ll to the 1970's Chicago does not celebrate the crime figures of the past. The many physical buildings & Sites have been torn down or white washed over of their former gangland glory. My tour will create a sense of the time periods with old locations & specifically buildings & haunts Of the characters of Chicago's past. I will set a tone that will take you back to the era by visiting neighborhoods & buildings from this time period. I will weave the stories of these characters into a physical scene of what times were like. A combination gangster tour with the architecturally significant buildings were all these nefarious Adventures took place. Recreating the time & place the events occurred. We will be immersed in the times by visiting old neighborhoods.

Recent Reviews

Beth W.United States
May 2026

Great overview of Chicago and its many neighborhoods - tales from the past to current culture. Bob left us wanting to come back and peel away another layer of each.

Martin V.United States
December 2024

Mr. Klunk is a wonderful tour guide. He is clearly knowledgeable on the topic of Chicago’s history. He is also very caring to his clients.

Your Chicago tour itinerary

The tour will be divided into Two periods : before WWll & after. Starting in the 1920's neighborhoods where the many events took place. Talking about the characters That participated in various gangland events & sites where they occurred. We will begin on the Northside of the city visiting old haunts, entertainment venues & very famous nightclub that has not changed since the 20's. A historic cemetery of the times resting place of characters That celebrates the era. We will see old hotels &. buildings from the era where events took place. We will see the theatre where a famous character was shot. I want to take you to an exhibit of nightclubs A neighborhood & restaurant that has not changed from those times. The Second period will take us to Chicago's Gold Coast & we will visit an exhibit of the famous nightclubs From the 50's 60's & early 70's. Ending at a Court House that was never torn down because Someone who was convicted of murder was to be hanged but he escaped & the hanging had to occur there!

Want to customize this tour?

Tell your guide which places matter to you, skip what doesn't, and tailor the experience for your group's needs. Not finding what you want? Message your guide to build something unique.

Transport details
Type: Private Transportation / Category: Minivan

Client will pick me up

What's included
Private Guide
What's not included
Other: Personal expenses.
Meeting location

Chicago, Illinois, United States

Airport: ,Cruise: ,ByGuide:

  • You can request a specific meeting location (for example, your hotel) during the checkout.
Other details
Tour categories
City Highlights
History
Off The Beaten Path
Tour reference number
1350139
Languages
English
Activity level
Minimal
Accessibility
Wheelchair Accessible

Traveller reviews

4.3

FAQs

Who is this private tour in Chicago best suited for?

This private tour in Chicago is perfect for history enthusiasts and those interested in the Prohibition era and gangster history. It's also ideal for travellers who want to explore architecturally significant buildings and immerse themselves in the stories of Chicago's past. The tour is wheelchair accessible, making it suitable for travellers with mobility needs.

What should I bring or wear?

Can this private tour in Chicago be customized to focus on what I want to see and skip places I've already visited?

How long is the tour, and can the start time or duration be adjusted?

Where does the tour start and end?

Is transportation included?

How much walking is involved, and is it suitable for kids, seniors, or travellers with mobility concerns?

What happens if a site is closed, crowded, or the weather changes?

What languages is this tour offered in?

AI-generated. Please confirm details with your guide

-
Hours icon 3 hours
Private transportation
Private tour for 1-3 people
Your party size

1

Tour date
View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later
-
Hours icon 3 hours
Private transportation
Private tour for 1-3 people
Your party size

1

Tour date
View our cancellation policiesUpgrade for total flexibility with Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later
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