Private tour in Chicago J Michael S

The Chicago Story - Private Half Day Tour

5.0

(11) 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 Any Reason 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 Any Reason Cancellation
Book with a depositSecure your tour today and pay your balance later

J. Michael S

5.0

Guide rating

17

Reviews

Tours delivered

7 hrs

Avg. response time

Welcome to Chicago and to Illinois! I am originally from Chicago and have lived in Illinois nearly all my life. I am also a veteran traveller, having spent significant time in all 50 states, plus in 15 countries throughout Europe, Central America, and Asia. I have major travel experience in Canada, Guatemala, Israel, Palestine, China, the Philippines, Great Britain, Spain, Portugal, Italy, and brief experiences in Jamaica, Switzerland, France, Mexico. I believe travel is about discovering stories and finding awe and beauty—everyplace we go. My best travelling experiences have come from discovering locals who can tell me the stories and show me the sights—out of their own joy and enthusiasm. As a part-time tour guide (for 20 years) my single aim is to share hospitality with those who have come to visit. Travellers are my guests. My hospitality consists of providing practical information—answering guests questions and meeting their needs while visiting, providing overall orientation, supplying transportation, sharing inside tips, customizing tours, and telling all the stories and anecdotes needed to make the places we visit come alive. When not giving tours, I am a writer (of humor) and a consultant to help non-profit organizations think strategically. My particular interest is history, particularly U. S. presidential history & sites, as well as migratory history. I am a curious guide; my academic degrees are in psychology, history, and religion. One of the greatest benefits of travel comes from finding common ground with people of differing beliefs and cultures. Chicago and its surrounding region is rich in both local and national history. The stories we share about our town and state help us understand the bigger pictures better—U. S. history, international migration, religious and cultural changes, economic progress and tragedy… I am eager to meet you, assist you in your visit, and exchange our stories and curiosities with each other. Bachelor's Degree in History (Southern Illinois University) Masters in Religion (Wesley Theological Seminary, Washington D.C.) Member of Chicago Tour Guide Professionals Association Published author (humorous memoir) Organizer of Church tours to Civil Rights Sites Hospitality Church tours for International Scholars (University of Illinois) Chicago, Milwaukee, St. Louis, Springfield Extensive travel in each of the 50 states in U.S. Organizer of International hospitality trips to Florida, Arizona, Yellowstone, California coast, New York City, Washington D.C., Philadelphia (from University of Illinois and Great Rivers Conference of the United Methodist Church) Operate a Consultation Business: strategy for non-profits. Drivers License from State of Illinois No restrictions for Chicago or anyplace in Illinois, Wisconsin, Missouri, Indiana, or Iowa.

Have a question or want to customize this tour? Message J. Michael S

Overview of your Chicago tour

The first part of our tour consists of a stroll in the Chicago loop, past sites that evoke stories about fires, immigrants, riots, political shenanigans, plus titans of industry and finance. I will share the story of how Chicago went from a city of only 300 people to over a million -in less than 70 years-. The last part of the tour includes a visit to the Chicago History Museum. I grew up near Chicago, and it was the centre of my universe. I watched Chicago TV and sports, read Chicago newspapers, and envied its size and wealth. Annual trips into the city were highlights of my early life. Chicago's ethnic tapestry, political dramas, and influence in American history were part of the reason I went on to earn academic degrees in history and religion. That scholarly background in turn has helped me continue to experience Chicago as a "lab" for my lifelong learning. I am eager for you to experience a slice of Chicago with someone who is in love with the people, the place, and the story. I'm your guide!

Recent Reviews

Emily P.United States
3 weeks ago

Mike was friendly, knowledgeable, and experienced. He adapted the tour to suit our interests and drove us to the spots we wanted to see. He provided cold water bottles. We learned so much about Chicago. Four hours was a a bit too long for us though. By the end, my brain was overwhelmed.

Cassi K.United States
July 2026

We enjoyed our tour. Micheal was lovely and personalized what we wanted to see.

David K.United States
December 2025

Bad weather meant that the original plan had to be changed. Mike did this effortlessly and seamlessly. Mike made the afternoon informative, entertaining, knowledgeable and engaging. Mike added lots of color to the local Chicago history. I will be recommending my friends to book a tour of Chicago with Mike.

Lauren R.United States
October 2025

We booked J. Michael (Mike) Smith as our Chicago tour guide as part of a 3-hour trolley ride for a management event. What a wonderful experience! He really took the time to learn about our group and planned a great itinerary with multiple stops. Mike was a wealth of information about the city and shared so many fun facts and stories! He was funny and held everyone’s attention the whole tour. He was extremely accommodating, went the extra mile to ensure we had the best time and was truly a joy to work with! We would highly recommend him to anyone looking for an amazing tour guide!

Paul O.United Kingdom
October 2025

Very personable and knowledgeable about his subject. We wanted a longer tour as our flight had been put back and Mike was very happy to accommodate our needs. Even with my limited mobility, he was able to show us and talk about all the major events. A really excellent tour and guide.

Cheryl M.United States
October 2025

Mike was an absolutely wonderful guide who assembled a full day that included areas that introduced to areas of Chicago that I did not see being offered by many others. Mike's background is diverse and pulls upon an amazing knowledge of history and literature that impressed all of us with how he folded it into an amazing day at the History Museum, Southside, Iconic Dining establishment, Wrigley Field, Al Capone's home, Emmett Till's home, Chicago Fire Stories, Food Referrals, and delivered well on our special requests that were off the beaten path. Not the least of which he picked us up from our hotel lobby and had beverages ready for the day! I would definitely reach out to Mike again. A day filled with great memories from a thoughtful, courteous, funny and smart guide! = )

Your Chicago tour itinerary

·We will begin in the Grand Hall of Chicago's Union Station--along with some stories of how the railroads helped make Chicago a centering for manufacturing and distribution. ·Then walking along the Chicago River, we will go past the Willis Tower (formerly the Sears Tower) and the Opera House. As we approach the curve in the river, we will be able to imagine stories from when Native Americans and French traders lived along the shores. As we step where the Wigwam was located, we'll share more stories of Abraham Lincoln. Moving along the riverfront, we'll see the building where the Kennedy money came from to elect JFK, pause to remember the victims of Chicago's worst disaster (it wasn't the fire.) And we will hear stories of some of Chicago's most famous and notorious citizens. ·Next, we'll travel by private car to the Chicago History Museum, where we'll be able to visualize the people & events we'd been pondering. The tour can be customized upon request and pick up & drop off can be arranged as well.

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: Other

The first part of the tour will be walking (1.5 miles) The second part will include private car transportation--a 2019 Subaru Outback, clean, with climate control, suitable for four passengers.

What's included
Private Guide
Tickets: tickets to the history museum
Private Transportation
What's not included
Food Drinks Snacks
Meeting location

Michigan Avenue, 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
Museums
History
Off The Beaten Path
Tour reference number
1314353
Languages
English
Activity level
Minimal

Traveller reviews

5.0

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 city's rich tapestry of stories, from its industrial rise to its political dramas. It's ideal for travellers who want to connect with a local like J. Michael S for deeper insights into Chicago's past.

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 4 hours
Private transportation
Private tour for 1-4 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 4 hours
Private transportation
Private tour for 1-4 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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