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10 Best Chicago Walking Tours | Windy City on Foot

10 Best Chicago Walking Tours | Windy City on Foot

Known for the interesting architecture and exceptional landmarks, the Windy City attracts people from across the globe. It is popular for specialty hot dogs, loyal sports fans, and delicious pizza. But getting the real feel of Chicago is not possible if you hit only the main attractions or you spend your trip in a single neighborhood.

The best way to get to know a city is on foot and you will get a chance to learn a lot on the walking tours. It helps to have a guide who is knowledgeable and can give information from an insider’s perspective.

If you want to get the perspective of a local, you should book a guided walking tour in Chicago. It will give you an insight into the real side of Chicago and will be an opportunity to explore it like a local.

"the bean" in Chigago

Best Walking Tours in Chicago, Illinois

1. Inside Chicago-Open your Eyes

This is a two-hour walking tour that will take you through the most famous Pedway in the city. The Pedway is an underground network of runners that connects more than 50 buildings. You will get a chance to see the hidden details in the architecture.

There is a 1-1.5 mile walk and you will be able to see the above-ground treasures like the 1920s-era church, Picasso statue, and a few buildings that are connected to the Pedway.

During this tour, the guides will share stories about the city which makes the tour very informative. The walks begin at 2 pm on Monday and Friday.

The cost is $30 for adults and $25 for seniors and children up to the age of 10. There are additional tours offered by Inside Chicago that take you into individual neighborhoods. 

2. Chicago Detours – The Histories Chicago Walking Bar Tour

Chicago Detours
Image by Chicago Detours

If you are keen to know more about the Prohibition-era history of Chicago, you should sign up for this 2-2.5 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.

At the various stops, you will get a chance to learn about Jazz music, Prohibition, and the most renowned architecture of the city. This is a must-do for one and all. Travelers enjoy the informative guides and get a chance to learn more about the different eras of Chicago.

The tours start at 5:45 PM on Thursday and Friday, at 2 pm on Saturday, and at 3 pm on Sunday. The tickets cost $36 and include snacks but not drinks. Besides this tour, there is an architecture tour and an 1893 World’s Fair tour. 

See Related: Is Chicago Safe to Visit?

3. Chicago Food Planet- Gateway to the West

Considered one of America’s best food destinations, Chicago attracts many food enthusiasts. If you want to sample the city’s best food, you should sign up for this walking tour.

The tastings will change but it usually includes pizza, doughnuts, Mexican, beer, hamburgers, and meatballs.

Rush Street - Chicago, Connors Park

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 samples for you to relish.

The tour availability will change seasonally but they usually start at 1 pm most days a week. The tour will last three hours and the tickets start at $60. You also have the option to upgrade the package to include three drink pairings for about $80 per person.

There are other tour options like Wrigleyville Brunch Crawl at Gallagher Way, Navy Pier Signature Food Tour, and Best in Chow Food Tour, amongst others. These tours are a great 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

Free tours by foot are ideal for those who want an in-depth overview of the famous Lincoln Park area in Chicago. The tour is a two-hour, 1-mile long walk that is very popular amongst the tourists.

There are excellent guides who will teach you about the history of the neighborhood and the 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 strains of the blue guitars from the music venues and pubs. You will be making stops at the Red Lion Pub, DePaul University, and many other landmarks.

This tour is very informative and you will enjoy seeing 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 Conservatory or the Lincoln Park Zoo.

This is a free tour but you can tip the guide whatever you want to at the end. The date and time of the tour will vary. Besides this tour, they also have tours of Millennium Park, and tours of the Riverwalk. 

See Related: Do You Need a Car in Chicago?

5. Chicago Gangsters and Ghosts Tour

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 1-1.5 mile walk.

You will get to explore old crime scenes and haunted locations where the city’s most famous crimes happened.

Your guide will be historian and you will learn the story behind all the details and the gangsters. The tour will be around the area of “The Loop” which was popular 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. You will be able to see crime scenes where it all occurred about a century ago. The tour is family-friendly and is not a theatrical guided tour but the stories are told in an intimate setting to give you a clear idea of the past of Chicago. 

Tour tickets start at $27 for adults and $25 for seniors aged 65 and above. Children below 6 can tour for free. The tours start at 11 am, 1 pm, 4 pm, and 8 pm daily. 

See Related: 12 Best Attractions in Chicago

6. Bobby’s Bike Hike- Culture walking tour and Chinatown Food tour

Enjoy your way through Chinatown on this tour with Bobby’s bike hike. The tour lasts for 2.5 hours and you will get a chance to savor delicacies that represent five different regions of China.

Chinatown is located next to the Loop on Cermak Street and Wentworth Avenue. It has colorful shops, restaurants, and impressive monuments. The guides will share the history of Chinese immigration to Chicago on the tour.

You can try hot pot, baked goods, dim sum, tea, and Szechuan chicken on the tour.

This tour is filled with incredible history and food. It is an opportunity for you to sample the culinary delights from different regions in China while you learn about the country. The price will be based on the day you choose to tour but it is around $55 for adults and $50 for kids.

The food samples are included in the price but you can upgrade to the VIP package to include samples of bubble tea, plum wine, and Chicago craft beer. 

The tours start at 4 pm on Friday and Saturday. They also have different Chicago river walking tours, sweets and dessert walking tour, and comedy and craft beer pub crawl of the old town. 

See Related: Best Day Trips from Chicago

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

This is a two-hour walking tour that will give insight into the history of Chicago from the late 1600s to the current day. It will discuss the Revolutionary War and the Eastland disaster of 1915.

On the tour, you will see the Chicago River, the Heald Square Monument, the Jewelers Building, Daley Place, the Chicago Cultural Center, and many other landmarks. The tour proceeds at a medium pace with knowledgeable and thoughtful guides.

Chicago River - Downtown Chicago

It is a free tour and you can choose to tip the guide whatever you want to. They also operate trips through Millennium Park and take you through the less touristy parts of the city.

There are a maximum of 20 people on the tour.

You can choose from 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 Loop Interior tour. 

8. Tastebud Tours

If you want to go on a tour to satisfy your craving for Chicago delicacies, this is the perfect Chicago walking tour for you. You will enjoy mouthwatering delicacies and learn about the city’s fine history.

Tastebud tours offer a World’s Fair-themed tour where you get to learn about the exciting and revolutionary time.

The most fun element of the tour is that it is led by a society member of the past, Bertha Palmer who is in the dress and character for the entire tour.

The tickets cost $78 and it includes entertainment and food. The tour lasts for 3 hours and runs on Friday and Saturday from May to October.

A very popular walking tour, the Taste of Chicago Food Tour is a three-hour tour that includes the best pizzas at Pizano’s Pizza followed by The Goddess and the baker, The Berghoff, Chicago Kernel, Fairy May Chocolates, and Pittsfield Cafe. There are also other tour options you can consider. 

See Related: Chicago CityPASS Review

9. Chicago Architecture Center’s Walking Tours

Apart from food, Chicago is also known for its excellent architecture with works from individuals like Frank Lloyd Wright and Daniel Burnham.

The center has an undisputed authority on the matter and they offer various walking tours that showcase the marvels around the city.

The tickets start at $15 and the tour is 1.5-2 hours long. If you want to know more about the history of skyscrapers in Chicago, you can choose a tour that is specially designed for it.

On the Historic skyscrapers tour, you will get a glimpse of the 19th-century marvels that have become an important part of the city today.

The guide will tell you about the innovations used to build them and how they have transformed the city with time.

The tour will last 1.5 hours and includes Burnham and Root’s Rookery designed by Frank Lloyd Wright the Marquette Building by Holabird and Roche and Auditorium Building by Adler and Sullivan.

Each building is an exceptional example of the details and decorations. Besides this, there are many other tours you can choose from.

See Related: 101 Hilarious Travel Puns

10. Bizarre Bucktown 

This walking tour is the perfect combination of magic and history. The tour guide is a neighborhood local who is easy to love. The tour lasts for 90 minutes and is one mile with a small group.

What makes the tour different from others is that the tour is personally created by the guide and he will take you through it. You will get a chance to learn about the mystery and history of the ghosts of Bucktown.

It is also a chance to see some of the haunted sites including the Bucktown Pub. The tour costs $15 per person and is available from Wednesday to Saturday. The Bizarre Wicket Park tour will take you into the world of the artists, the beer baron, the snake oil tycoon, mobsters, radicals, and the sister neighborhood.

Then there is a Bizarre 606 tour in the most unique park of Chicago, The 606. It is a self-guided walking tour of the history of the neighborhood.

Since there are small groups on the tour, it feels like a private tour. 

Whenever you head to Chicago, do not forget to register for the walking tours. There is nothing like exploring the city like a local.

During the tours, you will get to meet different travelers from across the world and the local guide will give information about the history, architecture, food, and life in Chicago.

Join in more than one tour if you have the time. If not, choose to be a part of the tour that covers the most popular landmarks in the city. 

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