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8 Chicago Walking Tours We Love

by Joshua Hirsch                                                                                                                                   4/7/2020

Chicago is described as “perhaps the most typically American place in America” by James Bryce in 1888. Chicago inspires the most creative innovators and minds compared to anywhere else on earth. It is perfect for its industrialism and its culture is unbeatable. Its uniqueness is not like London or Paris, it’s purely American from head to toe. 

A city that is there to live at night, Chicago is never short of industrialism and tourism which makes it incredibly popular amongst visitors and residents alike. If you’re reading this, you’re either living in Chicago or are visiting to simply find out the best things to do in Chicago. There’s nothing better than going on a walking tour to teach you new things about Chicago alongside enjoying the wonderful delights of the city. Even permanent citizens still find it difficult to explore almost everything within the Chicago neighborhood. Expect to be in Chicago for a long length of time if you’re a tourist, and you won’t be disappointed with the energy and passion of a busy yet incredible city that separates itself from many other American cities. Every walking tour is led by knowledgeable and experienced guides who are just as passionate to share the wonderful delights of Chicago to you as much as you’re willing to unravel yourself in it. 

Here are 8 of the most fun and inspiring Chicago walking tours we love:

a sanwich being held by a man with another in the background

Grab a bite and walk the city with a tour lead by Sidewalk Food Tours

Enjoy the Unique Taste of Chicago with Sidewalk Food Tours 


Nobody does a tour like a Sidewalk Food Tours! Chicago refuses to play second fiddle when it comes to the city’s famous culinary dishes. Its signature food dishes make Chicago a chosen city for exceptional and unique food choices. Experience some of Chicago’s most famous food hotspots such as deep pan pizza and Italian beef! Take the River North Food Tour and taste the bests of the bests including Chicago-style hot dogs, as you deep-dive into the atmosphere of the city. Sidewalk Food Tours guides you with some engaging and creative stories of food combined with the incredible culture the city has to offer.


Take an Enchanting Stroll Under the Lights with a the Chicago After Dark Tour by Inside Chicago Walking Tours


After an exhausting day visiting some of the most famous landmarks, tasting unique culinary dishes or taking in a spot of shopping, take a relaxing stroll under the night lights of Chicago with the Chicago After Dark Tour. As the sun begins to dawn and the sky becomes filled with stars and shining lights, take in another view of the pretty views of Chicago. You don’t need to take public transport. Simply slow down, enjoy the sweet sounds of live music and see the best night views Chicago has to offer. There are many museums and restaurants open after dark to keep the city buzzing as the night draws to a close. You may even catch some end-of-day firework displays to round the night off.

the top view of a set of stairs with people walking in each direction

Familiarize yourself with Chicago old and new with The Architecture Center’s Walking Tour

Enjoy Chicago’s Unique Architecture with The Architecture Center’s Walking Tour


Chicago isn’t just known for its awesome, creative and unique culinary dishes, but is also well known for its incredible and awe-inspiring architecture. Experience wonderful works from famous creators such as Daniel Burnham and Frank Lloyd Wright. Both were fond of architecture and urban design, something that the city has benefitted from to give Chicago a more sophisticated and attractive appeal to it. The Chicago Architecture Center tour provides the luxury of selecting over 85 architecture tours. Feast your eyes on the city’s incredible and iconic skyscrapers, elegant offices and hotels and legendary housing. The tour is expertly lead by enthusiastic volunteers ready to take you on river cruises and share some fascinating stories behind the iconic architectural buildings. You’ll learn how Chicago grew from being a small settlement into now one of the bigger cities known to man. The tours typically last for 90 minutes, with a descriptive overview of Chicago’s architecture and history.


Gaze at the Most Beautiful Landmarks and Sights with the Dazzling Interior Architecture of the Loop Tour with Chicago Detours


Explore the wonderful architectural sights of stunning interior spaces that you will never experience when simply passing by. When accompanied by our knowledgeable tour team, you’d be astonished by what you’ve missed out on seeing. Some of the more hidden gems of interior spaces will give you another view of the beautiful sight of Chicago. The beauty of buildings will amaze you. Chicago’s loop tour contains interior spaces of offices, courtrooms, retail spaces and all kinds of business. Behind the exterior is developed beauty. You will think twice about walking past buildings without having a glimpse of its incredible innovation. 

the storefront of a Chinese restaurant with a large lime green sign

Immerse yourself in the neighborhood of Chinatown with the Chinatown Walking Tour

Escape Busy Midtown and Experience China with a Difference With the Chinatown Walking Tour by Chinatown Tour Chicago


Nobody can leave without visiting Chinatown! Chinatown is a common neighborhood across many different countries in the world, and Chicago is no different. At the heart of the vibrant business district, Chinatown in Chicago has been around for decades and is one of the older neighborhoods, but it doesn’t mean that it hasn’t anything to offer. Whilst its one of the older neighborhoods, Chinatown has plenty of treats on offer. Walking along the stretch of Cermak Road and Wentworth Avenue. take in the vibrant and busy culture of the Chinatown locals. On your way, enjoy award-winning dim sum, feast on hand-made jewelry, enjoy exotic tea and much more. Chinatown also has its own mall filled with numerous cafes. As you step in, its picturesque setting and culture will help you fit right into its tradition. 


The front of a ground headstone that reads "Dean C. O'Banion. 1892 - 1924"

Run the streets like Al Capone and jump into a tour with Chicago Crime Tours

Realize Chicago’s Most Notorious Mobsters with any tour by Chicago Crime Tour


Discover mob hangouts of some of Chicago’s notorious gangsters within the Chicago Crime Tour. Escape the fast-paced city life and the grandeur of art and attractions and dive into a deeper, sinner and darker world of crime. Learn about some of Chicago’s most notorious gangsters within the city’s criminal underworld. Chicago has a rich history of crime and mobsters such as John Dillinger, an American gangster operating in the “Terror Gang” during the depression era, and the polish mobster Hymie Weiss, the leader of the Prohibition-era “North Side Gang” with links to well renown gangster Al Capone. There are many crime walking tours you can choose from. If you’re brave, you can even take the night bus tour and experience the feeling of trepidation and fear when stopping at the scene some of the city’s most heinous crimes. 


a large brick wall painted white with graffiti on it reading "True to you"

Look through the lense of a Chicago street artist while you make your way through on the Offbeat Street Art Tour

Explore the Historic and Artistic Creations with the Offbeat Street Art Tour


Some of the best artists in the world were housed in Chicago and no doubt they’ve left a footprint in the city with some of the more beautiful art creations. Take the Offbeat Street Art Tour in Logan Square, and appreciate the art that accompanies you on your walk across the city’s streets. You will see art creations behind a building or around a corner that highlights the incredible innovations of artists shared with the wider audience. The tour begins at Wicker Park with a historical background of how art in the city took off to become mainstream. The art isn’t so easy to find, and that’s the excitement because the tour involves walking through secret hideouts where you’ll be welcomed with standout creations. 

a small restaurant on the water with a patio and a city view to the right

Guide yourself through one of the most popular neighborhoods in Chicago on the Lincoln Park Walking Tour lead by GPSmyCity

Take in the Adventure with Walks Through the Largest Park in the City with The Lincoln Park Walking Tour by GPSmyCity


Lincoln Park boasts one of the largest parks in the city and is a coveted and adventurous place to live. Full of stunning architecture down Fullerton Avenue and beautiful boutiques down Armitage Avenue, you’ll be taken back by the beautiful scenery and attractions. If you want to chill and gaze in the sky around the beautiful scenery, take in the trendy fashion stores or even experience unique nightlife with exciting live theatre venues, there is always something happening at Lincoln Park day and night. At night, you can enjoy the pleasantries of live shows at the Biograph Theater. The public park was famously found in 1976 and dedicated to the author of The Wonderful Wizard of Oz, L. Frank Baum, who was also a resident of this trendy and stylish city. The tour will talk you through some of the more historical landmarks, such as visiting the character statues placed through the park. Every step you take, there is always something going on.


Final Thoughts…

Experience Chicago with a difference and have more reasons to fall in love with Chicago. With its incredible landmarks, sights, nightlife, unique culinary tastes and adventurous walks, there is always something to do in Chicago at every corner you turn. Chicago isn’t a city to visit once. Along every route, there is always something happening. Enjoy the pleasantries of one of the more happening cities in the United States today!