Walking Tours - Chicago

March 30, 2022

From the stunning architecture of the Sears Tower to the reflective beauty of the Bean, there is no better way to see this city than on foot.

From world-class luxury retail along the Magnificent Mile to soaring spins on the Navy Pier Ferris wheel, there are so many ways to experience the many attractions of Chicago. So follow along as we take you through the best Chicago walking tours!

Bite into a Chicago-style hot dog sans ketchup and prime that pedometer as we walk, eat, and sightsee our way through Windy City.

Chicago Food Tours

Chicago Favorites Food and Walking Tour

Unlock the history and origins of Chi-town's most iconic eats on this food-filled 2.5-hour walking tour. Your Chicago Favorites Food and Walking Tour* features a mile and a half of leisurely walking through the most picturesque streets of downtown Chicago. Munch on a cheesy slice of deep-dish pizza, marvel at the Chicago Riverwalk and snap a selfie in front of the city's most infamous marquee.

Bobby's Bike Hike has been leading nationally recognized tours for over 20 years, and their expert guides will pepper your trip with spicy flavors and Chicago facts. Witness the Wrigley Building, sip on sensational local suds, and learn why ketchup is verboten on a Chicago-style hot dog.

Chocoholics will be delighted to uncover the origins of the brownie and savor this decadent Chicago-born dessert at the luxurious Palmer House hotel. In addition to being the inventors of this sweet treat, the Palmer House also happens to be the longest continually-operating hotel in North America.

*Gratuities are not included in the tour price. However, a 15-20% tip is customary and appreciated. 

pizza topped with shirmps with cheese oozing in the bottom with a side of pickles paired with a pint of beer in Chicago, USA

photo credit: pixabay

Downtown Chicago Walking Pizza Tour

It would be positively criminal to visit the Second City without sampling the cheesy decadence of deep dish pizza. For all those skeptics, the Downtown Chicago Walking Pizza Tour is here to convince you that deep is the way to go! Escape into a world of pure pizza pleasure when you spend hours sampling every different style of slice.

Related Post: Ultimate Guide to Big Bus Tours - Chicago

From deep dish to grandma-style, Neapolitan, Roman, and everything in between, you will feast on all iterations of 'za. Your tour group's intimate size will allow you plenty of time to discuss the merits of each pizza variety.

Learn about the diverse cooking methods and wide range of ingredients as you frequent parlors from River North to Magnificent Mile. Leave your marinara-filled outing feeling full and fully versed in the incredible American evolution of pizza. 

Chicago's Chinatown Food and Walking Tour

Craving Cantonese, or perhaps a bite of Beijing-style duck? Chow down on a rainbow of Chinese delicacies when you reserve your spot on Chicago's Chinatown Food and Walking Tour.* Dive into Chicago's Chinatown food scene when you spend three hours strolling through this vibrant district.

Moan over mouthfuls of juicy dim sum dumplings, try native treats from the Xi'an region, or warm up with a steaming Szechuan hot pot. Beginning at the Chinatown Gate, you will set forth on a magical culinary journey through the diverse regions of China.

Related Post: Current Festivals and Events in Chicago

Test your spice tolerance with Sichuan chili peppers, cook your own meat, Mongolian style, or sip your traditional tea with a sweet portion of Portuguese tart. 

*Gratuities are not included in the tour price, and a $10 tip is suggested.

nightshot of cars passing under the Chicago Chinatown Gate in Chinatown, Chicago, Illinois, USA

photo credit: Chicago Chinatown via Facebook

Chicago Architecture Tours

Chicago Walking Tour: Art Deco Skyscrapers

Are you an art deco fan? Discover the unbelievable architecture and tumultuous history that makes the Windy City fascinating with the Chicago Walking Tour: Art Deco Skyscrapers.

Admire the artistic style and intricate designs of the Windy City's most iconic buildings as you stroll from the Rookery through the N LaSalle St building. Let your expert, certified guide regale you with inspiration for the city's architectural triumphs. Follow the evolution of Chicago's edifices from the stark and streamlined Jazz Age to more modern and simple.

Related Post: 32 Totally Free Things to Do in Chicago

Witness such great Chicago structures as 135 S LaSalle St or the Field Building, and don't forget to take a peek at the Chicago Architecture Center. While not directly included in the tour, your ticket will allow you admission to the galleries.

Riverwalk & North Loop Walking Tour

Stretch those feet and prepare for a sensational Chicago history refresher on this Riverwalk & North Loop Walking Tour*. This perennially popular free tour kicks off at the Du Sable Bridge and serves up searing Chicago River views. Admire the sparkling Riverwalk as you travel back to the 1670s and uncover the origins of this midwestern metropolis.

Take in the towering majesty of the Jewelers Building, stop by the Heald Square Monument, and soak in stories of the American Revolutionary War. Real history buffs will be chomping at the bit to show off their Eastland Disaster knowledge, while art lovers will be in awe over Picasso's public monument.

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Snap endless photos of the world's most extensive Tiffany Glass-domed roof. Then seek out the unique State of Illinois Building located in the Loop. This jam-packed tour will take almost two hours from start to finish and covers 1.7 miles of Windy City ground. 

*While this tour is free, gratuities are a great way to show your appreciation

night view of lights on bridge in along riverwalk in Chicago, Illinois, USA

resized image

Millennium Park & Michigan Ave Walking Tour

First-time Chi-town visitor? Check every last sight and landmark off your bucket list when you book a Millennium Park & Michigan Ave Walking Tour.* This completely free tour features the very best of Chicago from Cloud Gate to Buckingham Fountain.

Spend two hours admiring skyscrapers such as the Tribune Tower and the Wrigley Building. Listen up as your local guide spills intriguing tea, like the tale of the city's rebirth from out of the ashes of the Great Fire or the reversal of the River.

Gaze in awe at the Crown Fountain, and be sure to have that camera handy as you'll be dying to document this interactive public art and video sculpture for the 'gram.

*While this tour is free, gratuities are a great way to show your appreciation

a crowd of people around the interactive installation called the Crown Fountain located in Millenium Park with trees and buildings in background in Millenium Park, Illinois, Chicago, USA

photo credit: Millennium Park via Facebook

West Loop Tour: The Gateway

Gussy up your guided walk of the west loop with some extra special narration! Then, link up with Free Tours by Foot for the immersive West Loop Tour: The Gateway*.

Pay what you wish as you absorb the scenic views, cultural heritage, and film legacy of this easternmost section of the West Loop. Sip on a richly roasted coffee from the French Market, swoon over the south branch of the Chicago River, and clock in all 108 stories of the Willis Tower.

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Observe the opulence of the Civic Opera House and its famous connection to the film Citizen Kane. Next, study up on railway history with a stop at the breathtaking Great Hall inside Union Station. Finally, conclude your two-hour journey with a holy pilgrimage to the Old St. Patrick's Church. This stately place of worship happens to be the oldest public building to survive The Great Chicago Fire of 1871. 

*While this tour is free, gratuities are a great way to show your appreciation

Frank Lloyd Wright Home and Studio

Venture to Oak Park to tour the home and studio of one of America's most influential architects. Frank Lloyd Wright conceived the Prairie style and launched his groundbreaking career here.

This organic style of design featured an emphasis on flow. Being founded on the belief that we needed fewer, larger rooms. The Frank Lloyd Wright Home and Studio is a homage to Wright's vision of new American architecture. Tour his studio, where he designed over 150 projects, or wander around the historic neighborhood grounds.

Take in the drafting tables, Japanese prints, and casts of classical sculptures that inspired him and his team, or soak in some sunshine on an outdoor guided audio tour. Depending on which tour option you choose, tickets start at $15.

Ground view of the Frank Lloyd Wright House in the fall in Chicago, Illinois.

photo credit: Frank Lloyd Wright Home via Facebook

Ghost and History Tours

Gangsters and Ghosts Tour in Chicago

Gangsters, ghosts, and ghouls, oh my! Embrace Chi-town's dark past with a thoroughly haunted Gangsters and Ghosts Tour. Revel in the harrowing history of Chicago as you spend two hours traveling back to the 1920s.

This period of prohibition was the heyday for the Windy City. Bootleggers, gangsters, and the like were drawn to the famous Loop. Riddled with crime, 'the Loop' featured many secret underground tunnels and hidden speakeasies.

Related Post: 13 Must-See Famous Buildings in Chicago

Visit the real gangster hangouts of Al Capone. Then take a break at the Palmer House Hotel (rumored to be haunted). Finally, stroll through Death Alley.

However, lovers of the occult will be drawn to the otherworldly happenings at the Congress Hotel. Named one of the most haunted places in the State of Illinois. Try to see if you can spot Capone's ghost. He's said to frequent his old suite on the 8th floor!

abstract sculpture in the middle of flower bed and man on bench in the background at Julia Porter Park, Chicago, Ilinnois, USA

photo credit: Lyn Becker via FacebookWInd

Windy City Ghost Tour

Lincoln Park, after dark? Only if you dare! Muster up some courage and perhaps pack your anti-ghost spray as you prepare to take on a Windy City Ghost Tour.

Equal parts history and haunting, this one-hour evening event is designed to thrill. Immerse yourself in the macabre as you meander through burial grounds, spooky theaters, pubs, and more. Begin your journey on the ancient grounds of Julia Porter Park, built atop an old Civil War burial ground.

Next, set your sights on the creepy Alphawood Foundation, once the site of an insane asylum. Other incredible tour drops include the Red Lion Pub, the Biograph Theater, and Oz Park. Along your nocturnal journey, you will be serenaded with legends of gore and lore from Lincoln Park's unholy past. 

Related Post: 31 Unforgettable Romantic Things to Do in Chicago for Couples

Midwestern charm, a drool-worthy gourmet food scene, and scores of spellbinding architecture draw millions of visitors to Chicago each year. Whether you are marveling at the gothic style of the Tribune Tower or hightailing it to Chinatown for some delightful dim sum, there's no doubt that the Windy City demands a packed tour itinerary.

See even more of the Second City's world-class delights when you set forth on a guided walking tour. Gaze upon the designed genius of Frank Lloyd Wright's Rookery, or fill up your Instagram with prolific amounts of public art. From Picasso to deep-dish pies, Chi-town walking tours will leave you in complete wonder of the White City. 

Tell Us, What's Your Favorite Chicago Walking Tour?

Leave us a comment below!


isis with mural in background

Written By Isis Maya

A New York native, Isis-Maya spent most of her professional life working in TV production until a vacation whisked her away to Central America and her love o ...

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