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: Windy City Ghosts Haunted Walking Tour

2. 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: Underground Pedway & Downtown Secrets Walking Tour

3. 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: 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: Ultimate Food Walking Tour with Tastings

5. 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: Art Institute Skip-the-Line Tour with Guide

6. 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: 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 Underground Donut Tour

8. 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

9. 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: Treasures of the Golden Age Walking Tour

10. Chicago: Treasures of the Golden Age Walking Tour

This Historic Treasures of Chicago tour covers the most significant historic architectural landmarks in Chicago’s Loop. Your expert guide, trained by the Chicago Architecture Center, will focus on great cultural buildings from the late 19th and early 20th centuries, which harkened back to earlier time periods and were designed in revival styles such as Beaux Arts, neo-Georgian and neo-Gothic. Marvel at exteriors and interiors of dazzling beauty and startling originality, and get a glimpse inside some of the city's most beloved buildings.    The highlights of this walking tour will include the Chicago Cultural Center, home to the world's largest Tiffany dome; the iconic Marshall Field's department store, now Macy's on State; and the Palmer House, a beautifully restored hotel from the 1920s. 

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What people are saying about Chicago

Overall rating

4.7 / 5

based on 624 reviews

Lizzy, our guide was so sweet! You walk through the beautiful city, stop here and there and listen to interesting facts and stories. Halfway through there‘s a break for getting some brownies and using the bathroom. Would definetly recommend! Lizzy always made sure everybody has a great time and no one gets lost and stays with the group. Loved it!

Loved this tour! Our tour guide was wonderful and super knowledgeable and engaging. The history of Chicago was very intriguing and it was so nice to be able to get out and safely explore at night. Loved every bit of the gangster history! Would definitely recommend!

Awesome tour! Learned a lot about the city itself and prohibition. Furthermore, Kai the tour guide know really everything about the city and you could ask her everything! Thanks for the nice tour

Fun way to spend time in Chicago! It was easy to keep up with and hear our guide, and she led us to gems in the city we wouldn't have found otherwise!

Awesome tour filled with lots of interesting and cool factoids about Lincoln Park/Chicago! Definitely would recommend!!!