The 10 Best Walking Tours in Chicago, Illinois (IL)

February 1, 2022 Margarita Chappel

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. Chicago Loop Walking Tour

Chicago Cultural Center, 78 E Washington St, Chicago, IL 60602, USA Wild Onion Walks Chicago
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5.0 based on 27 reviews

The Loop is the heartbeat of downtown Chicago! It is filled with great architecture, drop-dead gorgeous interiors and fantastic works of art from famous artists. Along the way, we'll discuss some of the people, and people groups, that have helped to make this one of the "must see" communities, in Chicago!

Inclusions: Local guide

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

Reviewed By Carol Jean V

Amazing tour of this fascinating walkingtour of Chicago'sMagnificentMile. . My husband thought it would be about the retail shops, and was elated to find out this tour was more about Chicago's interesting history and the incredible architecture in this city. Kevin is an incredible historian, educator, and fantastic enthusiastic person. We highly endorse this walking tour.

2. Chicago Riverwalk Photo Shoot and Walking Tour

North LaSalle Street & West Wacker Drive, N LaSalle St & W Wacker Dr, Chicago, IL 60601, USA Wallflower Studios
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5.0 based on 1 reviews

Rather than taking selfies everywhere you go or trusting a stranger to take a picture for you, leave capturing the special moments to us. You will be escorted by a local professional photographer who will guide you through your chosen route and will take pictures of your experience so you can return home with the ultimate souvenir. Your photo tour includes: -Your choice of a 30 minute or 1-hour private tour with a professional photographer -High-resolution edited images delivered via a private online gallery within 1-2 days -Enjoy unlimited access to your photos and download as many as you would like with no expiration date *not all stops may be included depending on the length of time you select.

Inclusions: Private walking tour along Chicago's Riverwalk and the surrounding area, Professional photographer to take pictures of you throughout the tour, Private online gallery of edited images from your shoot delivered within one to two days

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Reviewed By knowluck44

I can't say enough great things about this adventure! Andrea was amazing in showing us different areas of the park we never would have found on our own. She did a wonderful job of taking fun, candid photos and was very professional (she even carried our stuff for us!). The photos are really great and we were able to pick our favorites to keep, even the quirky ones! Andrea was also super flexible and helped us decide what places we wanted to see or spend more time in. It may seem expensive, but for the professional photos and personal tour of the park, it was well worth it. This was a really great way to get the best of both worlds! It's a lot of walking, so make sure to wear comfy shoes. Thank you, Andrea!

3. Boston Walk Through History Private & All-Inclusive Tour

Tremont St opp Temple Pl, Boston, MA 02108, USA ForeverVacation Boston
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5.0 based on 1 reviews

Our Boston Walk Through History Tour will take you to the most historic spots in Boston in one day. If you are looking for a bit of delicious food, some great photos, and a ton of American History, then this is the tour for you. The morning will start with meeting with your friendly local guide. From there your tour will begin as you start your day walking through Boston and exploring the most historic landmarks in Boston. ==== Full schedule 9:00 AM- Meet your guide Park Street Station 9:15 AM- Arrive at Boston Common 9:30 AM- Arrive at Massachusetts State House 10:00 AM- Granary Burying Ground 10:20 AM- Mesmerizing Kings Chapel 10:45 AM- Learn about the Old South Meeting House 12:00 PM- Boston Massacre Site 12:15 PM- Lunch! 1:00 PM- Faneuil Hall Marketplace 1:30 PM- Go to Paul Revere's House 1:50 PM- The Old North Church 2:30 PM- Walk along Griffin’s Wharf 3:00 PM- Get dropped off by your guide at the Boston South Station

Inclusions: An Uber ride, English Speaking Tour Guide, All Fees and Taxes, Bottled water, Lunch

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Reviewed By Johnsavytravels6

Took this tour in early December as our last stop in the US. What a great tour and great food in Boston. Ask for Robin as your guide. She was so nice and answered all of our questions about Boston. Loved how this tour was private so we could go at our own pace. Highly recommend!

4. Private Frida & Friends tour in Pilsen

18th, Chicago, IL 60608, USA Chica-GO Off The Beaten Path Tours
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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

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)

6. 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

7. 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.

8. 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.

9. Windy City Ghost Tour

Julia Porter Park, N Halsted St &, W Fullerton Pkwy, Chicago, IL 60614, USA Windy City Ghosts
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4.9 based on 10 reviews

Windy City Ghosts walking Ghost Tour provides a look into the darkness that lurks below Chicago’s busy streets. Our Ghost Tour transports you back in time to an era of gangsters, bootleggers, bank robbers, and jazz babies. Windy City Ghosts nightly Ghost Tours take you through Lincoln Park, a beautiful North Side neighborhood with a twisted past. Learn about the forgotten burial ground that is the foundation of this bustling neighborhood. Check the bathroom mirrors in the Lion House of the Lincoln Park Zoo to make sure the ghost of a Victorian woman in white isn’t standing right behind you. Learn what spirit haunted Al Capone to the end of his days. On our Ghost Tour, you’ll hear the strange and disturbing tales associated with each of our carefully selected tour stops.

Inclusions: Professional and Courteous Guides, Intensely researched true stories of history, Documented accounts of hauntings and paranormal activity

Exclusions: Dinner, Motorized Transport

10. Chicago Loop Secret Food Tour with Private Tour Option

521 S Dearborn St, Chicago, IL 60605, USA Secret Food Tours Chicago
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4.9 based on 245 reviews

Join this 3-hour tour of Chicago's food scene, and see what sets this friendly mid-western metropolis apart. On this 12 person maximum walking tour of the 'Chicago Loop', a local guide will share with you some hidden gems and great stories about the city. Taste where the world-famous dipped Italian beef sandwich was invented, try some of the best deep dish Chicago pizza. Be shown how important the immigrants that built this town are to the food scene.

Inclusions: Food tasting, Local guide, Lunch

Exclusions: Hotel pickup and drop-off, Gratuities (option

Reviewed By ty_kormoz

I took my wife on this tour and Denise (our guide) was excellent and very knowledgeable about the history of every where we went. The conversation was natural and easy making the entire tour a confortable and relaxing experience

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