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11 Best Chicago Walking Tours | Windy City on Foot

11 Best Chicago Walking Tours | Windy City on Foot

Home to gorgeous landmarks and unique architecture, the Windy City (aka Chicago) attracts people from across the globe. It is famous for Chicago-style deep dish pizza, Chicago-style hot dogs, Italian beef sandwiches, jazz music, and loyal sports fans. 

If you want to get the real feel of Chicago, spending your time exploring only the main attractions or a single neighborhood is not enough. The best way to know a place in and out is on foot. Walking tours offer a chance for visitors to learn a lot about a city. The idea is to have a knowledgeable guide who can give information from an insider’s perspective. 

Experienced tour guides tailor walks to suit every fitness level and interest. To get an intimate perspective of Chicago, book tickets for a guided walking tour of the city. Walking tours will allow you to trot Chicago like a local and take an insight into the real side of Chicago. Here are the 11 best Chicago walking tours that can help you know the city and its people, culture, and traditions much better.

Best Chicago Walking Tours

1. Inside Chicago — Underground Pedway and Other Secrets of the Loop

Underground Pedway and Other Secrets of the Loop

Inside Chicago tours are the best way to explore Pedway, Chicago’s mysterious underground tunnel system. Connecting around 50 blocks in the loop, this two-hour walking tour will help you discover gorgeous architectural interiors. The Pedway is an incredible network of tunnels, bridges, and ground-level concourses connecting train stations, retail stores, hotels, and skyscrapers.

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. This tour will help you see the hidden side of Windy City. 

Covering around 1.5 miles on foot, this walk will also allow you to explore above-ground treasures, such as the famous Picasso sculpture, 1920s-era church, and buildings connected to the Pedway. The guide will share stories about the city throughout the tour, making it even more fascinating. You need to get a ticket beforehand to go on this tour. Inside Chicago also offers additional tours that will take you through different Chicago neighborhoods. 

2. Chicago Detours — Historic Chicago Walking Bar Tour

The Wrigley Building on Chicago Detours

If you’re keen to know more about the Prohibition-era history of Chicago, you should sign up for this 2 to 2.5-hour walking tour. You will be stopping for snacks and drinks at various places, including the Billy Goat Tavern, Jazz Age hotel, and a bar at a 19th Century mansion.

This evening tour is the best way to discover the legendary nightlife of downtown Chicago. You can explore architectural landmarks, historic sites, and other attractions, including the Chicago Water Tower, the Wrigley Building, and the Tribune Tower. 

At the various stops, you will get a chance to learn about Chicago history, Prohibition, Chicago breweries, and the world-renowned architecture of the city. Travelers enjoy the informative guides and get an opportunity to learn more about the different eras of Chicago.

Expect to walk at a leisurely pace, covering a half mile in about 2.5 hours, with plenty of time to stop for drinks and appetizers at three historic bars. The ticket cost includes snacks but not drinks. Besides this tour, there’s an architecture tour and the Chicago World’s Fair of 1893 Walking Tour

See Related: Is Chicago Safe to Visit?

3. Chicago Food Planet — Gateway to the West Loop Food Tour

Gateway to the West Loop Food Tour

Considered one of America’s best food destinations, Chicago attracts many food enthusiasts. If you’re looking to taste the city’s best food, you must sign up for this walking food tour. This tour will help you uncover the modern culinary delights and old-time industrial charm of the West Loop in this neighborhood. The food tastings change throughout but usually include favorites like old-fashioned donuts, meatballs, Roman pizza, hamburgers, and food & drink pairings. 

While you eat your way through the West Loop, the guides will share details about the history and culture of the neighborhood. There are plenty of food samples for you to relish. The tour lasts three hours, and the availability changes seasonally. Covering 0.6 miles, the tour guide will give you insights into the West Loop culture, history, and architecture. 

There are other public walking tours, such as Wrigleyville Brunch Crawl at Gallagher Way, Navy Pier Signature Food Tour, and Best in Chow Food Tour. These tours are an excellent option for food enthusiasts and families that want to explore the cuisine of Chicago. 

4. Free Tours by Foot — The Gangster Tour and Lincoln Park Blues

The Biograph Theater on Lincoln Avenue

Free Tours by Foot is ideal for people looking for an in-depth overview of the famous Lincoln Park area in Chicago. Their Lincoln Park Blues and Gangster Tour is a two-hour walking tour that includes a mile-long walk. The professional guides will tell you the history of Chicago’s neighborhoods and infamous gangsters. The area is famous for hot guitars, hidden gems, and hired guns.

You will walk through the footsteps of notorious gangsters and learn the impact of prohibition on Chicago. At 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, DePaul University, Biograph Theater, and other landmarks.

This tour is very informative, and you will enjoy exploring Lincoln Park with a guide. It will end at Lincoln Park, which the neighborhood is named after. You will only be a few steps away from the Lincoln Park Zoo or the Lincoln Park Conservatory. Though it’s a free tour, you can tip the guide at the end. The date and time of the tour will vary. Besides this tour, they also have Millennium Park and Riverwalk tours.

See Related: Do You Need a Car in Chicago?

5. Chicago Gangsters and Ghosts Tours

Chicago Gangsters and Ghosts Tours

Want to explore Chicago from the perspective of gangsters and ghosts? This guided tour is a lot of fun, and tourists praise the guides who mix humor with thrilling stories. It takes about two hours and is a 1.5-mile walk with a 20-minute break at a popular gangster hangout. 

You will get to explore old crime scenes and haunted sites in Chicago. Your guide will be a historian who will tell you the story behind all the details and gangsters. The tour will be around the area of The Loop, known as a vice district in the 1920s and 30s. It was a popular place for secret underground tunnels used by bootleggers, shady parting, deal-making, speakeasy saloons, and threats.

This is the place where the depiction of the 20th Century gangster began, with names like Al Capone and John Dillinger immortalized. You will be able to see crime scenes where it all occurred about a century ago. This family-friendly tour is not theatrical, but stories are told in an intimate setting to give you a clear idea of Chicago’s past. This 2-in-1 history-based tour is the best way to get the best of both worlds, i.e., Chicago’s ghost stories and gangsters. It is free for children ages 6 and below. 

See Related: Best Attractions in Chicago

6. Bobby’s Bike Hike — Culture Walking and Chinatown Food Tour

Culture Walking and Chinatown Food 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 & Wentworth Avenue. It has colorful shops, restaurants, impressive monuments, and delicious restaurants. 

If you want to taste the flavors of Chicago’s Chinatown, you must take this tour. This 2.5-hour tour is one mile long that gives you a chance to savor delicacies representing five different regions of China. You can try hot pot, baked goods, dim sum, tea, and Szechuan chicken. 

The professional guides of Bobby’s Bike Hike will share the history of Chinese immigration to Chicago while sampling China’s culinary delights. The ticket price depends on an individual’s age and includes all beverage and food samples. The VIP package includes bubble tea, plum wine, and Chicago craft beer samples.

Experience everything the Windy City is offering through your belly with this one of the best walking tours. The tour is ideal for those looking to know about the history of Chinese Americans, immigration to the Windy City, and Chicago arts and culture. Bobby’s Bike Hike also offers Chicago river walking tours, sweets & dessert walking tours, and the comedy & craft beer pub crawl of the old town.

See Related: Best Day Trips from Chicago

7. Free Chicago Walking Tours — Riverwalk and North Loop Tour

Chicago River - Downtown Chicago

Riverwalk and North Loop Tour by Free Chicago Walking Tours is a perfect blend of Chicago’s past, architecture, and incredible views along the Riverwalk. 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 tour, you will see the Chicago River, the Heald Square Monument, the Jewelers Building, Daley Plaza, the Chicago Cultural Center, Trump Tower, and other landmarks. The tour proceeds at a medium pace with knowledgeable and thoughtful guides.

The guide will tell you different stories, such as the beginning of Chicago, the Financiers of the American Revolutionary War, and the Eastland Disaster. Starting at the Du Sable Bridge and ending at the Chicago Cultural Center, the tour covers 1.7 miles on foot. There are a maximum of 20 people. Though the trip is free, you can tip the guide to show some appreciation. 

Free Chicago Walking Tours also operates trips through Millennium Park, taking you through the less touristy parts of the city. You can choose from the Lakefront Music and Arts tour, Loop and Public Art tour, Millennium Park tour, Off the grid tour, Riverwalk tour, Pedway Winter tour, Crime and Gangster tour, and the Loop Interior tour. 

8. Tastebud Tours — Chicago World’s Fair Food Tour

Goddess and the Baker on Chicago Worlds 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. Led by Bertha Honore Palmer, the Gold Coast Queen of Chicago, the tour will take you back to the 1893 World’s Fair. 

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

The ticket cost includes all food. You can shop and buy beverages or cocktails at locations along the way. They offer free cancellation up to 24 hours before the tour. 

Tastebud Tours also offers the Taste of Chicago Food Tour and Chicago Food and History Tour. Their Taste of Chicago Food Tour is three hours. The six stops are Pizano’s Pizza, the Goddess and the Baker, the Berghoff, Chicago Kernel, FannieMay Chocolates, and Pittsfield Cafe. 

Similarly, the Chicago Food and History Tour is a three-hour dinner tour. It can help you explore the food history of Chicago and taste quintessential dishes in Chicago’s Downtown Loop neighborhood.

See Related: Chicago CityPASS Review

9. Chicago Architecture Center Walking Tours

Burnham and Root's Rookery by Frank Lloyd Wright

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

From skyscrapers to historical treasures to other must-see attractions, there are several architectural tours to choose from. If you want to know more about the history of skyscrapers in Chicago, you can pick Chicago’s First Skyscrapers Tour

This 1.5-hour historic skyscrapers tour will give you a glimpse of some of the world’s earliest skyscrapers and 19th Century marvels. The tour’s highlights are Burnham and Root’s Rookery by Frank Lloyd Wright, the Marquette Building by Holabird and Roche, and the Auditorium Building by Adler and Sullivan. Each building is an exceptional example of unique details and decorations. 

The 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, Chicago Architecture Center offers other architecture tours that will take you through dozens of gorgeous buildings around the city. 

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10. Bizarre Bucktown 

Bizarre Bucktown Walking Tour

Bizarre Bucktown’s walking tour is the best combination of history, mystery, and ghosts. It will guide you through the western neighborhood of Chicago in a whole new way. On this 75-minute tour, Gordon Meyer, the tour guide, will discuss history, ghosts, and mystery while exploring Bucktown’s distinctive landmarks along the way. He will tell you about the scandals, hauntings, and murders on those quiet residential streets.

This one-mile walking tour is different from others because the guide has created it personally. Then, there’s the Bizarre Wicket Park tour. It will take you into the world of the beer baron, the snake oil tycoon, and the artists, mobsters, and radicals that shaped this neighborhood.

Another is the Bizarre 606 tour. It is a self-guided walking tour of obscure and strange history along the Wicker Park and Bucktown portion of the Bloomingdale Trail. Since it’s a small group tour, it feels like a private tour.

11. Free Tours by Foot — Self-Guided Chicago Walking Tours

Self Guided Chicago Walking Tours

Chicago is undoubtedly a world-class city, with a beautiful lakefront, outstanding architecture, great cultural institutions, and non-stop nightlife. Since it offers so much, it can be best seen on foot.

Free Tours by Foot has designed several self-guided walking tours focused on the city’s specific regions. You can go on these tours at your own pace. Some self-guided walking tours are The Navy Pier, Wicker Park, Millennium Park, Downtown Theater District, 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 the boardwalk. The south dock of Navy Pier is a 2,000-foot-long pedestrian boardwalk. This walking tour is open year-round with several theme park rides, restaurants, and entertainment venues along the beaten path. You can also go for other self-guided walking tours to make the most of your city tours.

Chicago Walking Tours: Book Your Tour Today

These are some of the best Chicago walking tours. If you’re heading to Chicago, do not forget to register for the walking tours. There is nothing like exploring the city like a local.

During these walking tours, you will get to meet different travelers from across the world. Also, you will learn about the history, architecture, food, and life in Chicago. 

I recommend that you join more than one tour if you have the time. If not, choose the tour that covers Chicago’s most famous landmarks. 

FAQs

What is the best time to visit Chicago?

The best times to plan a Chicago trip are April to May and September to October, as the temperature is pleasant and warm. Also, several festivals take place during these months, which will make your trip a memorable one.

How many days are enough for a Chicago trip?

Chicago offers so much to do and see to its visitors. Though there are countless things to explore, three to four days are enough to cover Chicago’s top attractions. The best idea is to plan before landing to make the most of your time in the city.

What is the best tour for first time visitors?

I recommend this Chicago Architecture Tour to see some of the best architecture in Chicago, including museums, the Harold Washington Library Center, and the Chicago Cultural Center.

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