Top Chicago Walking Tours

Chicago Architecture Tour: Underground Pedway and the Loop

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Discover the hidden gems of Chicago’s Loop area on a walking tour that showcases the best of the neighborhood’s stunning interiors and architectural must-sees. Step behind the facades to explore beautifully designed interiors—from art deco spaces to stained glass mosaics—as you follow a carefully curated route led by a guide. Along the way, learn about the city’s architecture, art, and history, and experience a side of Chicago often missed by travelers, all from a local’s perspective.

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Original Chicago Architecture Interiors Tour: Dazzling Interiors

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Immerse yourself in one of Chicago's most vibrant neighborhoods—and head off the tourist trail to discover sights and bites many visitors miss—on this small-group Chinatown food and walking tour. With your guide in the lead, learn about the cuisine of different regions of China, and discover the history of Chicago's Chinatown. Along the way, enjoy a generous array of tastings, from dim sum to Sichuan cuisine and beyond.

A picture of Chicago Chinatown’s landscape shows vibrant streets, iconic arches, and rich culture—everything guests explore on our Chinatown Food Tours. Food Tours in Chinatown bring it all to life.

Chicago's Chinatown Food and Walking Tour

Experience Chicago like a true insider on this top-rated walking tour that blends the city’s most iconic food, awe-inspiring architecture, and rich history — all in one unforgettable day. From deep-dish pizza to legendary skyscrapers, you’ll taste, see, and learn what makes the Windy City a world-class destination. Led by expert local guides and limited to just 12 guests, this immersive, small-group tour is the perfect way to discover the real Chicago — not just the tourist spots.

(755)

from US$80

Total Chicago: From Architecture to Food

Chicago in a Day Walking Tour: Food, History & Architecture

4 hours 30 minutesFree Cancellation

Price varies by group size

(1 331)

from US$101

Chicago Gangsters and Ghosts Walking Tour

We are the original, top-rated Gangsters and Ghosts tour! Hear the tales of the ghosts, and gangsters, that haunt the city. Explore the Chicago South Loop district with your historian guide, uncovering the many mysteries hidden behind every turn. Walk through Chicago's notorious South Loop, known as a vice district during the 1920s and 30s. Stroll through this now upmarket area of the city which was once home to underground speakeasies, secret tunnels, and bootleggers. Hear the true stories of Chicago's bloody past and the gangsters who caused havoc in the city. See the places notorious figures such as Al Capone used to party, make deals, and carry out "business". Discover the legends of the ghosts that are said to lure along the Chicago Riverwalk and the aptly named Death Alley. Stop at haunted locations including Palmer House, and the Chicago Theatre, before finishing outside the Congress Hotel, one of the most haunted places in Illinois.

Chicago Gangsters and Ghosts Walking Tour

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

4.8

(76)

from US$38

1 hour 30 minutesFree Cancellation

(336)

Eat your way through downtown Chicago on a walking food tour. Visit Millennium Park, the Palmer House Hotel, and other city landmarks and taste quintessential Chicago foods such as deep-dish pizza, hot dogs, and chocolate brownies. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. A bike or kayak rental is also included in the tour cost.

Taste deep-dish pizza, a Chicago-style hot dog, Italian beef, Garrett’s popcorn & the original 1893 brownie on our top-rated Chicago Food Tours—the ultimate Chicago Culinary Tour experience!

Chicago Favorites Ultimate Food and Walking Tour

We invite you to step inside the city’s most exclusive, jaw-dropping architectural treasures. Led by an expert local storyteller, you’ll discover breathtaking hidden spaces, from Frank Lloyd Wright’s sunlit masterpiece inside the Rookery to the world's largest Tiffany stained-glass domes at the Cultural Center and Marshall Field Building. Walk through the stunning Gilded Age luxury of the Palmer House and iconic movie backdrops along La Salle Street at a relaxed, conversational pace. We combine world-class history with photo vantage points, ending with personalized local recommendations. Don’t just see Chicago, experience it from the inside out.

(2 223)

from US$85

Chicago's Secret Interiors Architectural Walking Tour

Chicago's Secret Interiors Architectural Walking Tour

4.8

(18)

Chicago Architecture and True Crime History Tour

1 hour 30 minutes to 1 hour 45 minutesFree Cancellation

(525)

Chicago Walking Tour: Must-See Chicago

1 hour 30 minutesFree Cancellation

(156)

Taste some of Chicago's most iconic foods while walking through one of the Prohibition Era’s most fashionable and notorious neighborhoods. Learn about Chicago's world-famous cuisine and the gangsters who ate it all in one special unique tour! Sample two types of pizza - Chicago’s deep dish and historic tavern-style – as well as prime steak and the world famous “Chicago hot dog" all while treading the streets of Capone’s closest friends and dreaded enemies. Highlights include a visit to an old tunnel used by prohibition gangsters in the basement of one of the establishments; a mansion once used a a brothel for gangsters; the Cathedral where gangsters were gunned down by Capone’s men; and a restaurant owned by the man who brought down what was left of the Chicago mafia in the early 2000’s.

Chicago: Gangsters and Food Tasting Walking Tour

Chicago: Gangsters and Food Tasting Walking Tour

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

4.8

(17)

from US$80

Likely to Sell Out

Join us in the daytime or evening for City lights and breathtaking views

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

4.7

(3 449)

from US$28

Chicago Walking Tour: Historic Treasures of Chicago

Get an insider's introduction to Chicago's most celebrated buildings during this architecture-focused walking tour of Michigan Avenue, State Street, and the vibrant Loop area. Revisit the heyday of the skyscraper and visit stunning, art deco-era interiors, from the Palmer House Hotel to the Chicago Cultural Center. Admission to the Chicago Architecture Center is included, with an introduction by the docent.

Chicago Walking Tour: Historic Treasures of Chicago

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Chicago Crime, Mobsters & Ghosts Walking Tour

1 hour 30 minutes to 2 hoursFree Cancellation

4.7

(452)

from US$34

Likely to Sell Out

Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

Explore Chicago's buzzing food scene—and see some of its best-known landmarks on the way—on this two-in-one walking tour. The small group size offers are more intimate experience as you stroll around the vibrant Loop area, spotting highlights from the Willis Tower to the Rookery building. Indulge in a variety of famous Chicago foods, from deep-dish pizza to the world-famous dipped Italian beef sandwiches.

Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

Price varies by group size

(972)

from US$85

The Chicago Loop is the city's epicenter of culture, commerce, and design.

Discover the vibrant essence of Chicago with a self-guided tour through the Loop, the city’s historic downtown. This journey unveils a blend of striking skyscrapers and hidden architectural gems, allowing you to explore at your own pace. Uncover the rich history from the Great Fire of 1871 to the architectural masterpieces that define the skyline. Stroll past renowned theaters, museums, and captivating public art pieces that contribute to the city’s creative spirit. The Loop offers a unique perspective on Chicago's past and present, whether it's your first visit or a familiar stroll. — Self-guided exploration of Chicago’s historic Loop area — Learn about the city’s architectural innovations and history — Visit iconic landmarks like the Art Institute and Millennium Park — Perfect for first-time visitors or seasoned Chicagoans alike

Self-Guided Chicago Loop Tour Explore the City at Your Own Pace

2 hours to 2 hours 30 minutesFree Cancellation

Chicago Crime and Mob Bus Tour

(4)

from US$10

1 hour 30 minutes to 2 hoursFree Cancellation

4.6

(3 465)

from US$49

Special Offer

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

This walking tour is a feast for the eyes, combining art, architecture, and history as you navigate through bustling downtown Chicago. In a small group, you’ll marvel at skyscrapers and mosaic murals as you discover stories and secrets about the city’s past. See the stunning interiors and exteriors of noteworthy buildings and leave with a comprehensive understanding of the city’s downtown.

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

Lincoln Park Hauntings Ghost Investigation Tour

2 hours 15 minutesFree Cancellation

Discover a side of the Windy City that many visitors overlook—and immerse yourself in its vibrant street art scene—on this urban walking tour. With your art-expert guide in the lead, you can focus on soaking up the city's ambiance, and spotting artworks and murals you may not have discovered on your own. As you go, listen to in-depth commentary about the artists and artworks, and explore some of the city's hippest neighborhoods.

(47)

from US$40

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

Best Chinatown Food and Walking Tour in town! The Chicago’s Chinatown Food and Walking Tour is a 3-hour immersive culinary and cultural experience designed to highlight the unique tastes, rich history, and vibrant culture of Chicago’s Chinatown. This comprehensive tour combines a curated food-tasting journey with an exploration of iconic landmarks, making it the most enriching and flavorful Chinatown experience available in such a short duration. All of the restaurants and shops we pick for you are our member businesses of Chicago Chinatown Chamber of Commerce with guaranteed food quality and hospitality! You get the most of your money and time! A minimum of 4 participants is required for this experience. If the minimum is not met, the tour may be canceled, and you will receive a full refund.

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from US$40

Taste of Chicago's Chinatown Food Tours

Get to know the foodie Chicago neighborhood made famous by "The Bear"—and taste your way through some of the Windy City's best bites—on this small-group walking tour of River North. Visit locals-loved hotspots that represent the best of the city's dining scene, and Be sure to come hungry: You'll try everything from tacos and Italian beef sandwiches to deep-dish pizza, all while learning about the neighborhood's history and food culture.

(3)

from US$85

River North Food Walking Tour

Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel (with an enclosed and climate-controlled lounge) in the heart of the Magnificent Mile, and cruise along the Chicago River. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.

4.6

(95)

from US$89

Likely to Sell Out

Lake Michigan Sunset Cruise in Chicago

1 hour 30 minutesFree Cancellation

4.5

(1 635)

from US$45

Guide discussing A Sunday on La Grande Jatte

Skip-the-line: Art Institute of Chicago Guided Tour

2 hours 30 minutesFree Cancellation

Chicago City Minibus Tour

(587)

from US$84

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Top Attractions in Chicago

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What are people saying about Chicago

Patti_B, Jul 2026

Our tour guide Alan was...

Our tour guide Alan was wonderful l! We had a great overview of the the city without being rushed. Alan also recommended a place for pizza after the tour and dropped us off at the restaurant so we didn't need to walk. Would highly recommend this tour and hopefully you'll be lucky to have Alan as your guide.

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

Ambre_P, Jul 2026

Great guide and a cool way to see the city

Andre was one of the best walking tour guides that we’ve ever had and we’ve taken many tours across the states and Europe. His love for history, Chicago, and crime bosses was evident. Boring is not a word that would ever describe him! My 11 year old son loved talking to him and seriously wants to be BFFs with him! I highly recommend this tour!

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Kim_H, Jul 2026

Enjoyable tour of a few of Chicago’s Beauties

Kate was a knowledgeable and engaging guide who took us through five of Chicago’s best examples of Art Deco and postmodern architecture, spanning the 1890s through the 1980s. She pointed out fascinating details and shared fun facts at each stop. It was a great tour—we learned a lot and got to see stunning interiors that became some of our favorite memories from landmarks we’ve walked by often being an Illinoisan.

Chicago's Chinatown Food and Walking Tour

Lindsey_B, Jul 2026

Do it!!

We traveled to 5 different restaurants, all within very easy walking distance of each other. The food was absolutely phenomenal. Each place had something unique, so we never felt we were having multiples of anything. Our tour guide, Alex, was also nothing short of amazing. He was knowledgeable about Chinese food & culture, passionate in his delivery, and very personable. We would highly recommend this tour!

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

Colleen_M, Jul 2026

What a great way to tour a city!!!! Just do it!!

NOTE: because of weather the day before and trying to fit another event in that had gotten canceled the day before, I actually did the Ultimate City Tour with Bob's Bike shop. So though I cannot speak to the food on the food tour, I can at least say the tour I went on was excellent. I felt safe. My bike was in good working order, the group was fun. I ended up being one of the two the "Sweeps" For our ride and that was great. The tour guide DAN did a great job and was fun and informative. I have to say doing bicycle tours is a fabulous way to get some exercise, different fun and education while checking out places I travel to. Everyone at the shop was professional and fun. I did make a suggestion to them that maybe they have some excellent bike shop stickers for purchase. I buy them every place I go to so I can add them to my bike rack. Hopefully that happens! ❤️

Chicago Night Crimes Tour by Bus

Nicolette_R, Jun 2026

Best use of time, No Regrets!

The tour was amazing! I was happy to be driven around downtown area and learn of the various neighborhoods, in addition to the crime history. The tour guide and driver were wonderful! No comments or recommendations, very happy tourist! Can’t wait to come back and bring more riders! See you soon Chicago Crime Tours!

Chicago Walking Tour: Historic Treasures of Chicago

Laura_O, Jun 2026

Chicago Architecture Walking tour with Bill

After already doing the architecture tour by boat, I wanted to spend more time getting up and close with the buildings. Bill was a fantastic tour guide who shared so much knowledge and history about some of Chicago's most fascinating buildings. It was like a behind the scenes tour of Chicago that many visitors never experience. I learned so much about the cultural center and Tiffany's domes. Would highly recommend. Your ticket includes entry to the Chicago Architecture Museum, so we checked that out after the tour too.

Chicago Food Tour: 6 Dishes with Deep Dish Pizza & Beef Sandwich

JaNae_E, Jun 2026

A must do tour in Chitown

We do food tours wherever we go and this was one of the best tours we have been on! Sue was absolutely fantastic at guiding us through Chicago and giving us the perfect amount of history and interesting stories throughout the tour. The food was amazing and definitely will leave you full!

Chicago's Delicious Downtown Donut Tour with 8 Amazing Tastings

kberteaux, May 2026

No notes

Super great introduction to several amazing downtown bakeries. My favorite was the Tahitian vanilla donut at Firecakes, followed by the red velvet at Dan's. There were PLENTY of donuts and I left happy and fully sugared out. This covers a lot of over a mile of walking, FYI. And it ended exactly on time which I always appreciate.

Chicago Architecture Tour: Underground Pedway and the Loop

Jaydene_H, Apr 2026

Pedway through the Windy City

We had an amazing experience on the Chicago Architecture Pedway Tour, and a big part of that was thanks to our guide, Henry. He brought the city to life with fun and engaging facts about Chicago while leading us through the hidden underground pedway system—something we never would have discovered on our own if we hadn’t taken the tour. What really set Henry apart was his background in structural engineering. He seamlessly wove in technical insights that added a deeper layer of understanding to the architecture and infrastructure we were exploring, without ever making it feel overwhelming. It gave the tour a unique and enriching perspective. On top of that, I was genuinely impressed by his ability to memorize everyone’s name in the group—it made the experience feel much more personal and interactive. Overall, this tour was informative, unique, and incredibly well-led. Highly recommend it to anyone looking to experience a different side of Chicago!

Chicago City Tour with Architecture River Cruise Option

Krystal_M, Oct 2025

Fabulous time!

Best tour ever!!! Avery was FANTASTIC!!! I could have ridden around with him for hours hearing about the city. Hate that it only lasted 2 hours! He really knows his history and was able to answer every question I threw at him! Trevor give this man a raise! He was awesome and I would book you guys again based on my experience with Avery!