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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: Art Institute Skip-the-Line Tour with Guide

2. Chicago: Art Institute Skip-the-Line Tour with Guide

Experience a guided tour around some of the world’s greatest and most iconic art pieces at the Art Institute of Chicago. Avoid the crowds and lines and meet your expert guide at the Institute 30 minutes before opening time. Explore the expansive collection, learning more about both contemporary and classic pieces. Although the museum usually hosts 1.79 million people per year, you will be able to stroll among the pieces at leisure, getting up close and personal with works by famous and infamous artists like Edward Hopper, Pablo Picasso, Salvador Dali, and Andy Warhol. The Art Institute of Chicago is home to the greatest collection of Impressionist artwork in the world. Your guide will provide expert information on the collection and the museum’s history and hidden gems.

Chicago: Favorite Foods Guided Walking Tour

3. Chicago: Favorite Foods 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: Underground Pedway & Downtown Secrets Walking Tour

5. Chicago: Underground Pedway & Downtown Secrets Walking Tour

Come experience Chicago's famous "Pedway" – the mysterious underground tunnels downtown that keeps us all warm & dry in bad weather. Wandering the Pedway, through hidden corridors of stained glass and even underground swimming pools, you'll access interiors that seem to come up out of nowhere. In the first part of our 2-hour walk, on weekdays, you'll see beautiful and historic government building interiors, learning not only about the design and history of the buildings, but also about the movies filmed there. On weekends, as government buildings are closed, we instead explore a couple stunning interiors with stained glass mosaics that will leave you awe-struck. You'll walk under full blocks of buildings, up and down staircases, accessing these buildings through the Pedway's secret passages. In the second part of our walk, you'll discover some of the other "secrets of the Loop" hidden in plain sight. What is the meaning behind "The Bean"? What is the significance of Chicago and Route 66? How can someone walk right by a garden and not even SEE it -- or walk by a building and not see it, for that matter? You'll find so many secrets, packed into a leisurely 2-hour walk with your expert Chicago guide. Ending with a fabulous “secret” interior near the Art Institute, you’ll be in the perfect central spot for continuing your exploration of downtown Chicago on your own after the tour!

Chicago Underground Donut Tour

6. 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: Secret Food Tour

7. Chicago: Secret Food Tour

Sample the culinary delights of Chicago with the help of a fun and enthusiastic foodie guide. Be amazed by the city's eclectic mix of architecture and public art along the way. Taste delicious bites as you explore the city's central Loop district for 3 hours. Get better acquainted with what sets this friendly Midwest metropolis apart from other destinations and get a great insight into the art, architecture and everyday life in the city. Benefit from your guide's local knowledge and get tips to help you sightsee and explore the food and dining scene some more in your own time.

Chicago: Magnificent Mile Walking Tour

8. Chicago: Magnificent Mile Walking Tour

Start the tour by discovering how a dirt road known as Pine Street was transformed into a "Paris on the Prairie" and later into the Magnificent Mile - Chicago's premier shopping district. Hear the secrets and stories behind the striking buildings on North Michigan Avenue that have become architectural icons know around the world including the Tribune Tower, the Wrigley Building and 875 N. Michigan Ave. (formerly the Hancock Tower). Learn how the DuSable Bridge, built in the 1920s, transformed a warehouse and factory district into a commercial district. Find out how the street was further transformed with its wide avenue and Parisian style buildings, influenced by the world-renowned architect Daniel Burnham and the Plan of Chicago of 1909. Then, witness the street's final transformation into a high-end shopping and hotel district, becoming the shopping mecca that it still is today. Marvel at the vertical malls, skyscrapers, hotels, residential towers and buildings that were designed to embody the brands sold inside. Finally, enjoy admission to the Chicago Architecture Center included in the tour price where you can learn more about the various styles of architecture throughout Chicago. See an interactive model of the Downtown Buildings and models showing the development and many different styles of skyscrapers in Chicago.

Chicago: River North Walking Food Tour

9. Chicago: River North Walking Food Tour

Come enjoy the luxury and opulence of the Magnificent Mile and Gold Coast on this guided food tour, a tour through the historically affluent River North neighborhood. Explore the remarkable and historic River North neighborhood known for its extreme affluence, typified by the Magnificent Mile and the Gold Coast. Boasting Chicago's highest concentration of restaurants and art galleries, the River North neighborhood has become a favorite destination for foodies. You will taste foods from five unique restaurants and bakeries, and your food tour guides are experts not only at temporarily filling stomachs, but at plumping up tour-goers' local food knowledge too. This 3-hour walking tour offers a look into the history and culture of the neighborhood in between each of your 5 food tastings. While the stops are subject to change, we usually stop to taste at five of the following food places: • The Doughnut Vault (est. 2011): Food and Wine Magazine named it the best doughnut in America in 2012 • Lou Malnati's (est. 1971): Rudy Malnati is generally considered to be the inventor of Chicago deep-dish pizza • Xoco- (est. 2009): Top Chef Masters winner Rick Bayless is one of the best known chefs for Mexican cuisine in America • Iberico- (est. 1992): Serving you the most authentic tapas and regional specialties from all across Spain • Al's Beef- (est. 1938): Founder Al Ferrari invented the sandwich in Chicago's Little Italy back in 1938 • Fabcakes Bakery- (est. 2012): Delicious pastries inspired by the seasons Your informative guide will point out examples of historic architecture and beautiful public spaces that help make the River North neighborhood one of Chicago's most notable.

Windy City Ghosts: Hauntings of Chicago

10. Windy City Ghosts: Hauntings of Chicago

Meet your seasoned US Ghost Adventures 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.

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What people are saying about Chicago

Overall rating

4.7 / 5

based on 624 reviews

Great experience. The tour guide was very knowledgeable and friendly. The food was great too with many stories about it and the city. Highly recommend it.

Excellent tour! The tour guide was very knowledgeable of history and architecture of the city. The food choices were great!

Such a fantastic experience with our excellent guide Connor - could not fault the tour or the information

Was entertaining and Andrew gives a lot of emotion to is narrative which make it pretty nice

Ty was awesome! We really enjoyed the tour and would highly recommend it!