10 Best Walking Tours in Chicago, Illinois

Home to gorgeous landmarks and unique architecture, Chicago, the third-largest city in the United States, attracts people from across the globe. The city is famous for its insidious Prohibition history, deep-dish pizza, Chicago-style hot dogs, Italian beef sandwiches, jazz music, mobsters, and highly divided but loyal sports fans. That said: Cubs or White Sox?

If you want to experience the real Chicago, spending your time exploring only the main attractions or The Loop is not enough. The best way to know this place inside and out is to see it like the locals do — on foot. To get a more intimate perspective of Chicago, you’ll need to book tickets for a guided walking tour.

Walking tours offer a chance for visitors to learn a lot about our Windy City while experienced tour guides tailor walks to suit every fitness level and interest. Local guides will leave you with hints of their own experiences and, perhaps, some hidden gems to explore around this incredible city on the shores of Lake Michigan.

Best Chicago Walking Tours

Don’t let the idea of a walking tour deter you; Chicago isn’t as pedestrian packed as New York City. Unless you’re hanging out by The Bean in the middle of summer, you probably won’t be elbow-to-elbow with other tourists.

No matter when you decide to visit our fair city, here are the best Chicago walking tours that will help you understand the trials, tribulations, and triumphs of the Second City. Yes, Chicago has a lot of nicknames.

1. The Underground Pedway & Secrets of the Loop

Even longtime Chicagoans don’t necessarily know about the Pedway, especially if they don’t work downtown. The Pedway is Chicago’s kind of mysterious underground tunnel system, which connects around 40 blocks in the Loop. This two-hour walking tour will help you discover gorgeous architectural interiors. 

Walking in the Pedway, you will come across overlooked details, quirky stories, hidden passages, and rich symbolism that add texture and color to the overall narrative of the city. The Pedway is an incredible network of tunnels, bridges, and ground-level concourses connecting train stations, retail stores, hotels, and skyscrapers.

Covering around 1.5 miles on foot, this walk also allows you to explore above-ground treasures, such as the famous Picasso sculpture. Your tour guide will share stories about the city throughout the tour, making it even more fascinating. Plus, you get free cancellation as long as you cancel 24 hours ahead of time.

See Related: 15 Unique Places to Stay in Chicago, Illinois

2. Chicago Gangster and Food Walking Tour

If you’re keen to know more about the Prohibition-era history of Chicago, which was rife with mob activity, you should sign up for this 2 to 2.5-hour Chicago Gangter-themed walking tour. You will be stopping for snacks along the way, including the chance to have a Chicago dog at Mister J’s Dawg N’ Burger and lunch at Harry Caray’s Italian Steakhouse.

At the various stops, you will get a chance to learn about Chicago’s history, namely that of the days of Al Capone and the criminal underworld that ran the city. You’ll stop at various places that have a nefarious history of Prohibition.

Expect to walk at a leisurely pace, covering a mile in about two hours, with plenty of time to stop for drinks and appetizers. The ticket cost includes snacks but not drinks and offers free cancellation up to 24 hours in advance.

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3. Ultimate Chicago Food Tour: West Loop Neighborhood

Considered one of America’s best food destinations, Chicago is a favorite among food enthusiasts. If you’re looking to taste the city’s best food, you must sign up for this walking Chicago food tour around the trendy West Loop neighborhood which is one of the best Chicago neighborhoods for food. 

While you eat your way through the West Loop, the guides will share details about the history and culture of the neighborhood. Among your stops, you’ll try some deep-dish pizza at Lou Malnati’s and then enjoy dishes created by Michelin star and James Beard Award recipients.

You won’t do a ton of walking on this tour, so don’t worry too much about being too full from food tastings to wander. Don’t let that stop you from taking a look around the neighborhood yourself after this three-hour-long tour.

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4. Lincoln Park Blues and Gangster Tour

Free Tours by Foot is an underappreciated organization, especially in Chicago. The tours are free (but don’t forget to tip your incredible tour guide), which makes them great for budget-minded travelers. Their Lincoln Park Blues and Gangster Tour is a two-hour walking tour over a one-mile radius.

On this free tour, you will trace the footsteps of notorious Chicago gangsters and learn the impact of Prohibition on Chicago. In the Lincoln Avenue bar district, you can hear the strings of the blue guitars from the music venues and pubs. You will be stopping at the Red Lion Pub (one of my faves), DePaul University, Biograph Theater, and other landmarks.

This tour is very informative, and you will enjoy exploring Lincoln Park. It will end at Lincoln Park – the park that the neighborhood is named after. You will only be a few steps away from the Lincoln Park Zoo or the Lincoln Park Conservatory for more neighborhood adventures.

See Related: Chicago vs Detroit: What’s Better to Visit?

5. Chicago Gangsters and Ghosts Tour

In case you haven’t noticed, a lot of the Windy City history and architecture tours revolve around the city’s mobsters of old. Inside Chicago, these stories are numerous and fascinating — although sometimes a bit far-fetched. Luckily with this tour, you can trust that they’ve got their Chicago gangsters’ history down to a science.

This guided ghost tour is a lot of fun, and much of what you’ll learn is the city’s ghost stories with an in-depth overview of the criminal masterminds. It takes about two hours and is a 1.5-mile walk through old crime scenes and haunted sites like Death Alley, with a 20-minute break at the stunning Palmer House Hotel, which is the oldest continuously running hotel in the country. 

You’ll walk The Loop, which was infamous in the 1920s and 30s. It was a popular place for secret underground tunnels used by bootleggers and was full of speakeasies. This is the place where the depiction of the 20th-century gangster began, with names like Al Capone and John Dillinger immortalized.

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6. Chicago’s Chinatown Food and Walking Tour

Enjoy your way through Chicago’s Chinatown on this walking tour with Bobby’s Bike Hike. Chinatown is situated next to the Loop on Cermak Street and Wentworth Avenue. It has colorful shops, impressive monuments, and delicious restaurants. 

If you want to taste all the flavors of Chicago’s Chinatown in one shot, you must take this tour. This three-hour tour is only a few blocks long, giving you ample time to explore the rest of Chinatown after the tour.

The professional guides of Bobby’s Bike Hike will share the history of Chinese immigration to Chicago while sampling China’s culinary delights like duck and dumplings. Tickets include all beverage and food samples but not a gratuity and have free cancellation up to 24 hours in advance.

See Related: China Travel Guide: Tips for Visiting in 2023

7. Riverwalk and North Loop Tour

The Riverwalk and North Loop Tour by Free Chicago Walking Tours is a perfect way to get inside Chicago architecture from the outside. This two-hour walking tour will give insight into the history of Chicago from the late 1600s, including the Eastland Disaster of 1915.

On this family-friendly tour, you will see the Chicago River, the Heald Square Monument, the Jewelers Building, Daley Plaza, and other landmarks. As far as Chicago’s architecture tours go, you can’t get much better than a free tour around downtown Chicago.

Your Free Chicago Walking Tours guide will regale you with different stories from the beginning of Chicago. Starting at the Du Sable Bridge and ending at the Chicago Cultural Center, the tour covers 1.7 miles on foot. Please remember to tip your guide at the end of the tour!

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8. Chicago World’s Fair Food Tour

If you want to go on a tour to satisfy your craving for Chicago delicacies, Chicago World’s Fair Food Tour is the best option. Tastebud Tours operates trips highlighting Chicago history as well as its numerous food legacies, taking you back to the 1893 World’s Fair. 

Not only does the tour celebrate the exciting and revolutionary time, but it also serves up mouthwatering delicacies. This three-hour tour includes various stops, such as the Private Cliff Dwellers Club, Goddess and the Baker, the Berghoff, Chicago Kernel, and the Pittsfield Building. 

Get your hands on some delectable Chicago food while checking out Chicago’s downtown Loop neighborhood. This is one of the best walking tours for history buffs and foodies alike. The ticket cost includes all food, though you can shop and buy beverages or cocktails at locations along the way too. They offer free cancellation up to 24 hours before the tour. 

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9. Chicago: Treasures of the Golden Age Walking Tour

Besides food, Chicago is also known for its breathtaking architecture, with incredible work from renowned architects, including Frank Lloyd Wright and Daniel Burnham. The Chicago Architecture Center has an undisputed authority on the matter, and they offer various walking tours that showcase architecture around the city. 

But there are no Chicago tours that do as much justice to Chicago’s architectural history quite like the center’s architecture tour dedicated to the golden age. This architecture tour highlights buildings designed by noted architects Holabird and Roche, Daniel Burnham, and Louis Sullivan.

Tourgoers will visit the iconic Marshall Field’s department store, the Palmer House Hotel, and the Chicago Cultural Center, among others. Be sure to ask your guide about the Chicago flag design circa 1917 if they don’t explain it; it’s fascinating.

Your guide will tell you about the innovations used to construct these wondrous buildings and how they have transformed the city into a hub of skyscraper design and engineering. Additionally, the Chicago Architecture Center offers other architecture tours that will take you through dozens of gorgeous buildings around the city. 

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10. Self-Guided Chicago Walking Tours

Free Tours by Foot has designed several self-guided free tours focused on different Chicago neighborhoods to give you a better sense of this magnificent city. The best part of these tours is that you can go on them at your own pace.

Some of their self-guided walking tour options are Navy Pier, Wicker Park, Millennium Park, Old Town, and Wrigleyville. Each walking tour is different, with unique personalities and attractions.

For example, the Navy Pier is an incredible self-guided tour to experience the best of this 2,000-foot-long pedestrian boardwalk. This walking tour is open year-round, with several theme park rides you can access on the pier, restaurants, and entertainment venues along the way.

You can think of these city tours as Chicago detours – ways of seeing the city in a new light. Not exploring the same downtown streets, you’ll end your visit to Chicago with a greater appreciation for everything the city has been through.

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Related Resources:

• Where to Stay in Chicago: 11 Best Areas & Neighborhoods
• 30 Best Tourist Attractions in Chicago, Illinois
• 38 Unique & Unusual Things to Do in Chicago, Illinois