Location: Chicago
Top Things to do in Chicago
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Top 10 Historical & Heritage Tours in Chicago, Illinois (IL)
The windy city is a cornucopia of modern art, fine dining, cutting edge comedy, and die-hard sports fans. Snap a photo of your reflection in the silver Cloud Gate sculpture at Millennium Park before heading to Grant Park to get hit with the refreshing spray of Buckingham Fountain. There are dozens of museums and theater companies in Chicago, so a cultural experience is never hard to find. You’re sure to laugh your head off at the Second City Theater, the professional launch pad of many famous comedians.
Restaurants in Chicago
1. 2-Hour History of Chicago Architecture and Art Segway Tour
Overall Ratings
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
Overall Ratings
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
Overall Ratings
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. Private Frida & Friends tour in Pilsen
Overall Ratings
5.0 based on 2 reviews
Discover Pilsen and its local art, street art, food and people. We will visit a traditional bakery and taqueria and enjoy the art of many great local artists. And then there are the hundreds of cool murals in the neighborhood. We may even meet one of the street artists or stop by an artist studio (on request).
Inclusions: Masks and sanitizer are provided if needed
Exclusions: CTA tickets (please provide tickets yourself) , Gratuities
Reviewed By mdgnaperville
We had a wonderful walking tour with Leentje, partly in areas we knew, but never knew the great stories behind it, and partly in new areas. Although living close by, we learned so much, the kids of 11 and 9 asked so many questions, and loved the tour which had so many cool elements for them and us. Thank you so much Leentje!
5. Art Institute of Chicago Private Guided Tour with Skip-the-Line Ticket
Overall Ratings
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)
6. Chicago Architecture Walking Tour: Dazzling Interiors of the Loop
Overall Ratings
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
7. Chicago Lakefront and Museum Campus Small Group Tour
Overall Ratings
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.
8. 2-Hour Guided Segway Tour of Chicago
Overall Ratings
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
9. Chicago in a Day: Food, History and Architecture Combo Tour
Overall Ratings
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.
10. 2-Hour Chicago Lakefront and Museum Campus Segway Tour
Overall Ratings
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!
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