Private tour in Chicago Bob K

Half day ,Driving Tour of Oak Park & Surrounding Area

4.9

(16) reviews

-
Hours icon 4 hours
Private transportation
Private tour for 1-4 people
Your party size

1

Tour date
View our cancellation policiesUpgrade for total flexibility with Last-Minute Cancellation
Book with a depositSecure your tour today and pay your balance later
-
Hours icon 4 hours
Private transportation
Private tour for 1-4 people
Your party size

1

View our cancellation policiesUpgrade for total flexibility with Last-Minute Cancellation
Book with a depositSecure your tour today and pay your balance later

Bob K.

4.9

Guide rating

115

Reviews

Tours delivered

7 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

In 1848, the railway was extended west to Oak Park, ushering in the beginnings of this area covered by Oak trees & home to the Potawatomi Indian. In 1870 it was known as ' Saints Rest' because of all the churches. In 1902 it became a town. Frank Lloyd Wright & Hemingway were born here in 1899. We will visit the home of Hemingway but concentrate on Frank Lloyd Wright & his amazing influence on the town. We will walk the surrounding streets sprinkled with many homes built at various stages of his career including the magnificent Unity Temple. Visit the historic downtown, discovering why it is called 'Worlds Largest Village' and given the designation ' All American City'. Home to diversity in its population, it proudly says ' A Place to live. . . a way of Life'.

Recent Reviews

Linda S.United States
1 week ago

Bob is very knowledgeable and entertaining. We highly recommend him and the Oak Park tour.

Hanna R.United States
June 2026

It was wonderful trip Bob was very professional with a lot of knowledge and also very friendly You need to have more tour guides like him

Kimberly F.Cayman Islands
May 2026

The Oak Park and Frank Lloyd Wright home tour with Bob was fantastic. The highlight of our week long trip to Chicago. Truly! Bob is a Chicagoan and knows every building to and from Oak Park (and I'm sure beyond). He's an artist himself and knows a plethora of information about architecture and the art scene in the past and present. Well, actually about any scene in Chicago. You will enjoy his warm Chicagoan welcome and knowledge of his city. I highly recommend booking Bob.

Janet C.United States
October 2025

Although some locations were not open, this tour of the FL Wright home and studio was terrific. Bob was so imformative and personable. We highly recommend his service.

Kathy J.United States
September 2025

I highly recommend booking a tour with Bob! He is very personable, knowledgeable (he’s also an artist) and entertaining! Learned so much about Frank Lloyd Wright on our trip to Oak Park. Driving back got some beautiful pics inside the Garfield Park Conservatory and then drove around the Gold Coast. Had a lovely time!

Kasey H.United States
September 2025

I had the most amazing day with Bob! He was delightful and informative and showed me all the historic sites I had on my list! It was a wonderful 11/10 day in Chicago for this historic preservation nut!

Your Chicago tour itinerary

I will pick you up in my rental car at a prearranged location. We will all drive the 20 minutes to Oak Park. I will go over the itinerary & points of interest along the way. We will first visit Hemingway's house & look inside. Next we will arrive at The Frank Lloyd Wright Studio for the tour. Afterwards I will take you around the adjoining neighborhood for a look at the many other homes he designed over the years. We will see his Unity Temple , recently restored. From here we will visit the charming town . On the way back we will take in Garfield Conservatory( for an additional $10 fee ; you can experience one of largest & beautiful indoor gardens. Created by Jens Jensen ,prairie landscape architect.. & the historic park & buildings in an area of the same name. Driving back into the city under one of the few remaining elevated train, while filling you in about the surrounding area.

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: Sedan

We will tour in a sedan

What's included
Private Guide
Private Transportation
Tickets: Frank Lloyd Wright
What's not included
Other: Personal expenses.
Food Drinks Snacks
Tastings
Private Transportation With Driver
Equipment
Public Transportation
Classes Workshop
Accommodation
Services
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
History
Architecture
Tour reference number
832186
Languages
English
Activity level
Minimal

Traveller reviews

4.9

FAQs

Who is this private tour in Chicago best suited for?

This private tour is perfect for travellers interested in architecture, history, and culture. You'll explore the works of Frank Lloyd Wright and visit Hemingway's home, making it ideal for those who appreciate literary and architectural history. It's also great for anyone looking to connect with a local expert like Bob K. for deeper insights into the area.

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?

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 4 hours
Private transportation
Private tour for 1-4 people
Your party size

1

Tour date
View our cancellation policiesUpgrade for total flexibility with Last-Minute Cancellation
Book with a depositSecure your tour today and pay your balance later
-
Hours icon 4 hours
Private transportation
Private tour for 1-4 people
Your party size

1

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