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Chicago

Walking tours

Our most recommended Chicago Walking tours

Chicago: Gangsters and Ghosts 2-Hour Walking Tour

1. Chicago: Gangsters and Ghosts 2-Hour Walking Tour

See a different side of Chicago on a family-friendly guided tour and hear the tales of the ghosts that haunt the city. Explore the famous Chicago Loop district with interesting stories hidden behind each turn. Embark along the Chicago Loop, known as the vice district during the 1920s and 30s. See the places where gangsters such as Al Capone used to party, make deals, and carry out business. Visit haunted locations and old crime scenes led by historians. Stop at the Congress Hotel, Death Alley, and the Palmer House. Enjoy a refreshment along with way, with frequent stops and a restroom break.

Chicago Underground Donut Tour

2. Chicago Underground Donut Tour

Take a donut tour of the windy city, and discover the best Chicago has to offer. At each location, you will taste a curated sample of the best donuts. Some of the stops on this downtown tour include Stan's Donuts, Do-Rite Donuts, and Firecakes Donuts, true donut institutions. This two hour walking tour is led by a passionate donut expert who will guide you to some of Chicago's best donut locales. This tour caters to all size groups, both large and small. The donut tour is great for bachelor and bachelorette parties, birthdays, family reunions, weekend getaways, or even corporate events. There are two versions of the Donut Tour: The Classic Downtown Tour, as well as a local neighborhood tour in Wicker Park. Both are great options if you're excited about donuts. It really just depends on what neighborhood you want to explore: if you want to stay downtown or if you want to venture out to the Wicker Park & Bucktown neighborhoods to see how "the locals do it". In either case, don't hesitate to join the tour. Buy your tickets today!

Chicago Food Tasting: 2.5-Hour Guided Walking Tour

3. Chicago Food Tasting: 2.5-Hour Guided Walking Tour

Combine an enjoyable walk around Chicago's downtown to see some of the city’s top sites with stops to sample some of the city’s famous tastes. On this 2.5-hour guided walk, you'll get to taste the foods Chicago is best known for doing right. Enjoy deep-dish pizza, the original Italian pastries, Chicago-style hot dog, and a classic Italian beef sandwich. Enjoy a VIP craft beer sample for an additional fee. Along the way, you’ll see some of Chicago's most iconic spots including Millennium Park, the Chicago Riverwalk, the Art Institute, and the famous Bean. By the end of the tour, your stomach will be full of delicious food and your head will be full of fascinating knowledge about Chicago. During the colder months, the tour makes use of the unique underground Pedway system that connects much of downtown and keeps you warm and cozy. On warmer days, you’ll walk at street level to enjoy the large promenades of the loop. The leisurely walking pace is suitable for people of all fitness levels.

Chicago: 2.5-Hour Taste of Chinatown Food Walking Tour

4. Chicago: 2.5-Hour Taste of Chinatown Food Walking Tour

Explore the complex layers of Chinese culture and the many contributions these people have made to both Chicago and the world. And what better way to show off Chinese culture then through food? Your guide will take the confusion and language barrier away as you sample your way through a variety of Chinatown's best restaurants and well-kept secret recipes. Start your tour at Phoenix Restaurant and begin with some yummy dim sum dumplings and a traditional Chinese tea tasting. Next, it will be time for a sweet treat - buttery custard tarts from Chinatown's oldest bakery. Then, try a unique and delicious spicy meat sandwich from the Xi'an region. Afterward, stroll through the charming Chinatown Square with its ethnic grocery stores and souvenir shops. Finally, taste a sampling of succulent dry chili chicken, followed by the famous spicy Szechuan hot pot. You'll have traveled all over China but only walked a few blocks on this delicious tour of one of Chicago's most fascinating neighborhoods.

Chicago: Windy City Ghosts Haunted Walking Tour

5. Chicago: Windy City Ghosts Haunted Walking Tour

Meet your guide at the meeting point then set off on an unforgettable walking tour through Northside Chicago. Travel back in time as you visit some of the city’s most haunted locations in the mysterious Lincoln Park neighborhood. Learn about the forgotten burial ground that forms the foundation of this bustling district. Check out the bathroom mirrors at Lincoln Park Zoo, home to the ghost of a Victorian woman in white. And, hear about the spirit that haunted Al Capone in his final days.  Throughout the tour, you’ll listen to the strange and disturbing tales of each location. On the standard tour, visit eight historic sites, or opt for the extended tour which includes 12 ghoulish locations. By the end of the tour you’ll have learned about and experienced firsthand the alternative side of Chicago.

Chicago: Ultimate Food Walking Tour with Tastings

6. Chicago: Ultimate Food Walking Tour with Tastings

Your Chicago food tour will take you through the River North neighborhood — the original Chicago foodie destination — to sample some world-famous Chicago dishes, local favorites, and sweet treats. Choose between a shared group or private tour. Start with a very well-known Chicago dish: the Chicago-style hot dog. Perfect for summers at a baseball game (cheering on the Cubs or Sox of course), or for a quick lunch on a workday, this local take on a hot dog is a debate-worthy food in Chicago and is taken very seriously by locals. You will also sample the world-famous Chicago deep-dish pizza! An entire meal unto itself, this staple of the Chicago food scene originated in River North in the 1940s when workers and families needed filling dishes at low prices.  After you’ve filled up on pizza and hot dogs, continue your tasting journey with a classic Chicago sandwich: Italian beef. This hearty meal came about during the Depression, and it’s here to stay. Conclude your Chicago foodie experience here, with easy access to the ‘L’. Even if you say you’ll never be hungry again, don’t forget to note some great dinner recommendations from your guide.

Chicago: History, Culture and Architecture Walking Tour

7. Chicago: History, Culture and Architecture Walking Tour

Start your tour under the dazzling marquee of the Chicago Theater (which you might recognize from the movie-musical Chicago) before heading off into the bustling city. Your first stop is inside one of the best-preserved spaces built for shopping in Chicago, featuring an unforgettable atrium at its core. Then head towards the Chicago Pedway, a uniquely Chicago feature used by locals and commuters daily to move about the city in a network of underground tunnels. Afterward, head back above-ground near City Hall and head inside to see the classic interior design and architecture. Next, enjoy a sweet treat, and local tradition: Chicago-style popcorn. Weather permitting, take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings, including Marina Towers, the Britannica Building, and the Willis Tower. From there, make your way to another delicious destination. Along the way, enjoy views of the world-famous Wrigley Building and the incredible Chicago Tribune building, the heart of Chicago’s thriving and historic journalism industry. Your second tasty confection is locally made chocolate from a Chicago staple. Finally, take a stroll through the beautiful lakefront parks along Michigan Avenue. Round up your tour in the picturesque Millennium Park, home to the iconic Bean sculpture. Here, your guide will conclude your tour and point you in the right direction toward more amazing sights, great lunch spots, or drink recommendations.

Best of Chicago: Skydeck, River Cruise & City Walking Tour

8. Best of Chicago: Skydeck, River Cruise & City Walking Tour

At Willis Tower, take the first elevator of the day up 103 floors to the Skydeck, the 3rd tallest building in the Western Hemisphere. On a clear day views extend to 4 States!! Back on ground level, it’s time to traverse Chicago’s Loop, alongside your local guide and see the city’s Art Deco architecture will be laid out before – or rather, above – you! Pass the magnificent Board of Trade Building and take in the statue of Ceres, Ancient Greek goddess of the harvest, looming over the skyline three stories high. The Loop may be a business district but it’s much more than that—including the birthplace of the world’s first skyscraper. At the Monadnock Building where your expert local guide will be waiting to take you on a journey through the city’s most storied structures Next, walk through the awe-inspiring lobby designed by Frank Lloyd Wright at the Rookery. Many elements here only an expert can point out, including the secret glass mosaics adorning the lobbies. You’ll listen to the history of the cast of characters that brought Chicago to world-wide fame, admire one of the world’s most historically significant doors and get a view of the largest Tiffany glass dome in the world. Millennium Park is the next stop where the iconic Cloud Gate can be found. After getting a picture in front of ‘The Bean’, it’s time to walk up Michigan Avenue for more architectural stories and history. The last stop of the day is Chicago’s iconic Riverwalk for a 90-minute architecture cruise, passing down the Chicago River and Lake Michigan. Enjoy the snacks and refreshments available to purchase on board, and take in the day’s discoveries from the water.

Chicago: Deep-Dish Pizza and Local Food Walking Tour

9. Chicago: Deep-Dish Pizza and Local Food Walking Tour

Immerse yourself in an exploration of Chicago’s outstanding food culture. Navigate through the Loop district, which is buzzing with activity, as your guide brings you straight to the vendors and restaurants they love most. Taste some of the local staples, including the world-famous deep dish pizza. Pass by iconic places like the Chicago Riverwalk and get to grips with the evolution of the city, as immigrants brought their culinary influence from all over the world. Get to know family shops owned for generations and learn the origins behind the Windy City's most beloved street eats. Enjoy a local street food staple, perhaps the famous Chicago-style hot dog or Italian beef sandwich. And, of course, a food tour of Chicago is not complete without a bite of the iconic deep-dish pizza. Try a slice and top it off with a traditional sweet treat for a complete foodie experience.

Chicago: Riverwalk Self-Guided Walking Tour

10. Chicago: Riverwalk Self-Guided Walking Tour

Learn about Chicago's history, culture, and architecture on a self-guided tour via an app. Enjoy animated videos allowing you to visualize what you cannot see, such as snapshots from different centuries or interior rooms. Start by downloading the app that will function as your personal guide, audio tour, and map all in one (download instructions received via email after booking). After downloading the app, head to the starting point of the tour at McCormick Bridgehouse & Chicago River Museum. As you being to walk, spot the DuSable Bridge and learn about the iconic terracotta Wrigley Building. From there, head west and pass Wabash Bridge, once voted America’s Most Beautiful Bridge. After that, see the Chicago Vietnam Veterans Memorial, a tribute to the soldiers who lost their lives during the Vietnam War. Next, stop by the 600-foot Marina Towers. Learn how these towers function as a “city within a city.” Head to the Dearborn Street Bridge and hear why an angry mob once gathered here with axes. Listen to the tale of one of the strangest and deadliest shipwrecks in American history. Learn how a devastating shipwreck happened on a river only 20-feet deep. Continue on toward the Merchandise Mart, a gorgeous example of Art Deco architecture. Learn how the Chicago River helped this city go from a small settlement to a bustling hub of culture and commerce. Next, arrive at Wolf Point, where Chicago’s very first hotel stood almost 200 years ago. Dig into the era when this place was little more than a wild frontier, then head back the way you came for the final section of the tour. Stop at the Tribune Tower containing pieces of historic buildings from across the world, including the Notre Dame Cathedral and the Berlin Wall. Next, come face to face with NBC’s Chicago headquarters, modeled after the famous skyscraper at 30 Rockefeller Center. Finally, arrive at the last bridge separating the Chicago River from Lake Michigan, where the tour concludes. Take in the soothing scenery and snap a few photos for your Instagram.

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Frequently asked questions about Chicago Walking tours

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Other Sightseeing Options in Chicago

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What people are saying about Chicago

Dash was a very good tour guide - he was highly knowledgeable about the architecture and history of downtown Chicago, and his enthusiasm made it even better! He took me inside buildings that I would have never assumed to go inside. I felt as though I was really being shown around by a local expert

AMAZING! Dylan our tour guide made the day so much fun! The food was amazing and I was so full by the end of the tour but completely satisfied. As a solo traveler I couldn’t rate it anymore.

This was a great tour to learn a bit more about Chicago’s history. Our guide, Andre, was incredible!

We had a great tour, Baylor was our guide and so informative and friendly!! Highly recommend 5star!

Our guide leader was very animated and seemed to love telling us about the history of the City.