10 Historical & Heritage Tours in Illinois That You Shouldn't Miss

October 25, 2021 Cedrick Jardin

Discover the best top things to do in Illinois, United States including 2-Hour History of Chicago Architecture and Art Segway Tour, Private Al Capone Gangster Tour in Chicago, Private Segway Tour of Chicago, Art Institute of Chicago Private Guided Tour with Skip-the-Line Ticket, Chicago Architecture Walking Tour: Dazzling Interiors of the Loop, Chicago Lakefront and Museum Campus Small Group Tour, 2-Hour Guided Segway Tour of Chicago, Chicago in a Day: Food, History and Architecture Combo Tour, 2-Hour Chicago Lakefront and Museum Campus Segway Tour, Lonely Planet Experiences: River North Historical Food Tour.
Restaurants in Illinois

1. 2-Hour History of Chicago Architecture and Art Segway Tour

300 E Monroe St, Chicago, IL 60601, USA Absolutely Chicago Segway Tours
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5.0 based on 15 reviews

See Chicago’s landmark architecture, outdoor sculptures and famous skyline by Segway! This family-friendly guided tour is both an exciting and educational way to explore Chicago. Plus, you'll save your feet from a day of walking and instead, quickly glide along the lakefront soaking in views of the spectacular skyline while seeing some of the tallest buildings in the world.

Inclusions: Segway tour, Professional guide, Thorough Segway orientation from a certified Segway trainer, Helmet and a bag on the Segway to store personal belongings

Exclusions: Gratuities

Reviewed By 355ron

We were in Chicago just for the weekend from Michigan. We decided to do the 2 hour lakeside tour and are so glad we did. it's a great excursion and our 13 year olds loved it. Our tour guide Cedar was really knowledgable and a joy to be around.

2. Private Al Capone Gangster Tour in Chicago

Chicago Private Tours and Productions
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5.0 based on 2 reviews

Chicago and the history of the mob are synonymous when we look back at history. That’s why we provide an in-depth Chicago Gangster Tour that makes all of the infamous stops for our patrons.  Visit the old stomping grounds of: • Al Capone • John Dillinger • The Untouchables View crime scenes immortalized in vintage news footage, the theater where the law caught up with Dillinger, the restaurant where the North Side Gang riddled Al Capone’s motorcade with rounds from their Tommy Guns, and the site of the St. Valentine’s Day Massacre. We bring Chicago’s true crime past to life before your very eyes.

Inclusions: Hotel pickup and drop-off, Transport by private vehicle

Exclusions: Gratuities

Reviewed By 768marthah

We took the private architecture tour of Chicago Private Tours and Productions on 11/22/19. Stevie did not disappoint. His depth of knowledge and storytelling ability made us feel like Al Capone himself was in the Empire room with us. We learned about the history and saw the interiors of the most amazing buildings while being driven to the curb by chauffeur Carmela. Learned about the history of skyscrapers, Union Stock Yard, the World’s Fair in 1893 and it was so interesting that I bought “The Devil and the White City” for the plane ride home. Stevie even added a quick stop at Harry Carey’s so we could see the secret underground tunnel to the courthouse - used at a time when corruption reigned in the city. This tour was my favorite part of the weekend in Chicago and I highly recommend.

3. Private Segway Tour of Chicago

300 E Monroe St, Chicago, IL 60601, USA Absolutely Chicago Segway Tours
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5.0 based on 1 reviews

There's no better way to tour the world-class city of Chicago than on a Segway! On your very own private tour, we will cruise around the parks and along Michigan avenue and show you the best that Chicago has to offer. If you are passionate about history, architecture, hauntings, Al Capone, and gangster or more, just let us know! We will customize the tour to fit your interests!

Inclusions: Use of Segway, Helmet

Exclusions: Gratuity , Enterence into museums, We do not enter into buidlings on our outdoor adventure

Reviewed By 355ron

We were in Chicago just for the weekend from Michigan. We decided to do the 2 hour lakeside tour and are so glad we did. it's a great excursion and our 13 year olds loved it. Our tour guide Cedar was really knowledgable and a joy to be around.

4. Art Institute of Chicago Private Guided Tour with Skip-the-Line Ticket

The Art Institute of Chicago, 111 S Michigan Ave, Chicago, IL 60603, USA Babylon Tours Chicago
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5.0 based on 1 reviews

The Art Institute of Chicago attracts nearly as many visitors as other leading galleries like the Met, Louvre & British Museum. On this 2 to 2.5 hour private guided museum tour, you’ll be able to skip the line and explore it’s most famous pieces with the help of an engaging guide who will lead the way. Highlights Generally Include: (if artwork is not on loan or being restored etc.) Paris Street, Rainy Day by Gustave Caillebotte Sunday on La Grande Jatte - Georges Seurat Sky Above Clouds - Georgia O'Keefe Nighthawks - Edward Hopper A Picture of Dorian Gray - Ivan Albright America Windows - Marc Chagall The Old Guitarist - Pablo Picasso Inventions of Monsters - Salvador Dali Four Mona Lisas - Andy Warhol

Inclusions: Skip-the-Line Private Museum Tour , Professional Tour Guide Exclusively For You , Duration 2 - 2.5 Hours , Wheelchair Friendly, All Entrance Fees

Exclusions: Tour price does NOT include hotel pickup or drop-off (we recommend UBER or Taxi), Tour price does NOT include gratuities (optional)

5. Chicago Architecture Walking Tour: Dazzling Interiors of the Loop

425 S Financial Pl, Chicago, IL 60605, USA Inside Chicago Walking Tours
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5.0 based on 221 reviews

Explore some of the most stunning interior spaces you’ll ever see – spaces you’d surely pass by without a second glance if you weren’t shown them by a seasoned, in-the-know tour guide. Ranging from stained glass mosaics from the turn of the century to soaring Art Deco spaces from the Roaring 20s, these spaces are some of the most beautiful in the city -- and open to us to explore!

Inclusions: Local guide

Exclusions: Gratuities

Reviewed By Lois331

Wonderful tour .. very informative..live in Chicago and still learned a great deal .. have taken many Chicago tours and this was the best

6. Chicago Lakefront and Museum Campus Small Group Tour

300 E Monroe St, Chicago, IL 60601, USA Absolutely Chicago Segway Tours
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5.0 based on 134 reviews

Looking for fun things to do in Chicago? Look no further - Explore Chicago with one of our professional guides on this scenic 7 or 8 mile Chicago Segway tour. Begin these guided Chicago Segway tours traveling through the fragrant garden paths of Grant Park to view Buckingham Fountain. Enjoy the breeze as you glide effortlessly to the most popular Chicago tourist attractions along the Chicago lakefront: the Museum Campus, the Shedd Aquarium, the Field Museum, and of course Soldier Field, home of the Chicago Bears. You can't go wrong with this perfect sightseeing tour.

Inclusions: Professional guide, Use of helmet, Use of Segway, Training and Practice

Exclusions: Gratuities, Food and drinks, Hotel pickup and drop-off

Reviewed By 355ron

We were in Chicago just for the weekend from Michigan. We decided to do the 2 hour lakeside tour and are so glad we did. it's a great excursion and our 13 year olds loved it. Our tour guide Cedar was really knowledgable and a joy to be around.

7. 2-Hour Guided Segway Tour of Chicago

2 E 8th St, Chicago, IL 60605, USA Segway Experience of Chicago
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5.0 based on 72 reviews

2 hours of being a kid again!!! Take a Segway tour with us and discover how beautiful Chicago truly is. Ride through some of Chicago's most popular destinations with an experienced guide. We will glide through scenic and historic downtown Chicago and explore the beautiful Grant Park, around the Buckingham Fountain, near the Museum Campus and near the lakefront. Or take our Riverwalk tour to explore the Chicago River to view Navy Pier and famous Chicago bridges, traveling up historic Michigan Avenue and passing by Millennium Park. No matter which tour you choose, it will be a memory lasting a lifetime!

Inclusions: 2 hour guided Segway Tour of Chicago, IL

Exclusions: Gratuity for Tour Guide, Does not include meals

Reviewed By abdulrR2163GB

this is my view ident there with my hoverboard and it said so fun and then you should have called you back downtown to go look at people and the people riding hoverboards thank you for watching myAll 4 without having an account atAll 4 without having account every

8. Chicago in a Day: Food, History and Architecture Combo Tour

The Chicago Theatre, 175 N State St, Chicago, IL 60601, USA Chicago Urban Adventures
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4.9 based on 76 reviews

Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epic tour of some of the city’s greatest hits: incredible architecture both old and new, delicious local treats and iconic Chicago dishes, a uniquely Chicago transit ride, stunning river views and much more! Marvel at the stunning Chicago skyline and discover why Chicago’s architecture is among the best in the world Get around The Loop like a local: at street level, underground, elevated rails or perhaps even on the water Enjoy a couple of classic made-in-Chicago snacks like Chicago-style popcorn and homemade chocolate Get a taste for Chicago’s most famous food in one of the city’s most historic neighborhoods Discover why locals have so much passion for their Chicago-style classics

Inclusions: Professional Local Guide, Popcorn Tasting, Chocolate Tasting, Water Taxi or Subway Ticket, Chicago-style hot dog, Deep dish pizza, Italian Beef

Exclusions: Gratuity

Reviewed By gramma P

If you only have one day in Chicago, are able to walk about 6 miles, enjoy facts about history and architecture, and want a taste of the food Chicago is known for, be sure to go on this tour. Our guide was knowledgeable and interesting to listen to and we thoroughly enjoyed our day in the city.

9. 2-Hour Chicago Lakefront and Museum Campus Segway Tour

300 E Monroe St, Chicago, IL 60601, USA Absolutely Chicago Segway Tours
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4.9 based on 84 reviews

Looking for fun things to do in Chicago? Look no further - Explore Chicago with one of our professional guides on this scenic 7 or 8 mile Chicago Segway tour. Begin these guided Chicago Segway tours traveling through the fragrant garden paths of Grant Park to view Buckingham Fountain. Enjoy the breeze as you glide effortlessly to the most popular Chicago tourist attractions along the Chicago lakefront: the Museum Campus, the Shedd Aquarium, the Field Museum, and of course Soldier Field, home of the Chicago Bears. You can't go wrong with this perfect sightseeing tour.

Inclusions: Professional guide, Use of helmet, Use of Segway, Training and Practice

Exclusions: Gratuities, Food and drinks, Hotel pickup and drop-off

Reviewed By 436jacik

My husband and I took this tour and had a blast! Tammy was absolutely fabulous! She was knowledgeable and funny and bubbly and so wonderful to spend the afternoon with. We enjoyed the information she shared and the jokes that went along with it. We recommend this tour for everyone! It was an exciting and beautiful way to see some of the highlights of Chicago. We got some awesome pictures of the skyline too!

10. Lonely Planet Experiences: River North Historical Food Tour

806 N Michigan Ave, Chicago, IL 60611, USA Chicago Urban Adventures
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4.9 based on 11 reviews

Experience the best travel stories for yourself! Join a local expert and uncover hidden gems on this Lonely Planet Experience powered by Urban Adventures. Join us for the ultimate foodie adventure in Chicago’s historic River North area alongside a local guide who can show you the best spots for some of the city’s best loved dishes. From deep dish pizza to Chicago-style hot dogs, this tour will leave you filled with delicious local foods as well as some insider knowledge into the city’s culinary history and culture.

Inclusions: Local, English-speaking guide, Chicago-style Hot Dog, Deep Dish Pizza, Italian Beef

Exclusions: Gratuity

Reviewed By W9455DVsamr

I had a wonderful time with the tour. If I could rate it 10 starts I would! The meeting point was super easy to find, and there was no trouble in getting everyone together and started on time. The tour was great as it walked you around downtown Chicago getting to see things like the theaters, skyscrapers, and parks that the city has to offer. Another great thing was it was an architecture and food walking tour which let you taste everything that Chicago is known for like its. But on top of the respect to time, the well thought out route, and the food locations picked, it wouldn't have been near as great if it wasn't for my guide Wallach. Wallach is an exceptional guide and very knowledgeable in everything there is to know about the city. He was responsive to questions and always had a positive attitude throughout the tour. He also made sure the group stuck together and that no one was not engaged with the conversations that were being had. It was for sure an amazing tour and it would not have been amazing if it wasn't for Wallach. If I ever return to Chicago, I would definitely try to get a tour with Wallach again. And if you are planning a tour with this company, see if you can get Wallach on your tour, you won't regret it.

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