Top Chicago Walking Tours

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

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

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.

Chicago Favorites Ultimate Food and Walking Tour

3 hoursFree Cancellation

Explore the hidden side of Downtown Chicago—and see sights that even many locals miss—on a small-group walking tour of the Pedway (an underground network of tunnels that connects Chicago buildings) and the vibrant Loop. Ideal for architecture fans, this tour includes insider stories and landmarks you wouldn't spot on your own—plus a chance to see Windy City icons like the Picasso Statue and Millennium Park.

Chicago Architecture Tour: Underground Pedway and the Loop

Haunted Chicago: Crime, Ghosts, and Capone 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.

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

4 hours 30 minutesFree Cancellation

Price varies by group size

Chicago Architecture and True Crime: Halloween Edition

1 hour 30 minutes to 1 hour 45 minutesFree Cancellation

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

3 hoursFree Cancellation

Price varies by group size

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

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

Enjoy the opportunity to go behind-the-scenes at one of the Windy City's most storied venues on this insider tour of the Chicago Theater. Let your guide lead the way, as you hear about the theater's architecture, history, and famous performers throughout the years. Stand on the famed stage and take in the atmosphere, and see artist signatures from notable performers, including Frank Sinatra and Dolly Parton. A great activity for fans of music and live performance.

Likely to Sell Out

The Chicago Theatre Tour Experience

1 hour to 1 hour 15 minutes

4.0

(58)

from $32

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

3 hoursFree Cancellation

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.

Chicago's Secret Interiors Architectural Walking Tour

Discover one of Chicago’s top architectural marvels when you explore Frank Lloyd Wright’s UNESCO-listed Frederick C. Robie House, located right on the University of Chicago’s campus. Considered a masterpiece of Prairie School architecture, the building is famed for its cantilevered roof and rich wood details. Save money when you book tickets to the house in advance; call ahead to reserve a space on one of the museum’s frequent, small-group public tours.

Frank Lloyd Wright Robie House Admission

1 hourFree Cancellation

Travel through architectural history on this express, small-group walking tour, which covers Chicago's most famous buildings in chronological order (and which is speedy enough to cater to the most time-pressed travelers). With a guide in the lead, there's no need to fuss over maps or worry about directions. Simply stroll along and listen to the in-depth commentary on Chicago's architectural history; you'll learn about each building, and will have plenty of chances to stop for photos.

Chicago Walking Tour: A Walk Through Time

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 Chicago’s deep dish – 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 as 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. Gluten-free/vegan/vegetarian options are available (please reach out prior to the tour to inform us of any dietary requirements.)

Chicago: Gangsters and Food Tasting Walking Tour

Haunted Chicago Booze and Boos Ghost Walking Tour

2 hours 30 minutesFree Cancellation

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

2 hours 30 minutesFree Cancellation

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.

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

Get to know the Windy City the easy and comfortable way on a small-group minibus tour. Instead of long walks and navigating public transit, see major landmarks like Museum Campus, Buckingham Fountain, the Magnificent Mile, and Millennium Park from an uncrowded minibus with large picture windows. Your driver and guide knows where to find all the best views, and there are plenty of photo stops along the way.

Chicago City Minibus Tour

Chicago Haunted Interior Architecture Ghost Tour

1 hour 30 minutes to 1 hour 45 minutesFree Cancellation

Chicago Crime, Mobsters & Ghosts Walking Tour

1 hour 30 minutes to 2 hoursFree Cancellation

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.

Lake Michigan Sunset Cruise in 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

Chicago's Chinatown Food and Walking Tour

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Must-Dos in Chicago

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What are people saying about Chicago

Vanessa_S, Sept 2026

If you're looking for...

If you're looking for something fun to do in Chicago, check out the Taste of Chinatown Food & Walking Tour run by Bobby's Bike Hike. My husband and I had a great time trying different foods accompanied with interesting food/restaurant/area information. Lillian was a fantastic guide, and I highly recommend!

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

Laura_T, Sept 2026

Fun and informative!

A great way to see some of the highlights and beautiful architecture in the city. Also love that the train is included for us country folk who have never had that experience ;) Great food choices for the food tour at the end. Rich shared a lot of interesting facts and in a fun, easy going way! He was an excellent tour guide!!!!! Would highly recommend this excursion!

Chicago Architecture Tour: Underground Pedway and the Loop

James_F, Sept 2026

Great tour!

My daughter and I took the Chicago Architecture Tour: Underground Pedway & Secrets of the Loop this Tuesday while we were downtown for the day. We’re from the suburbs but had never heard about the pedway, so we figured it might be interesting. Our tour guide, Heath, was an outstanding! He was able to weave Chicago history, people, architecture, and artwork into a captivating tour about the pedway. Without him, we would have gotten lost in the pedway and had no idea about why it is so special and unique. We have walked away with a new understanding of what makes Chicago “Chicago”, and received some cool dining, drink, and shopping recommendations along the way. We highly recommend this tour if you have the time.

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

Jan_B, Sept 2026

Great intro to the food and history of Chicago

This was an easy biking 3 1/2 hour tour for the evening tour. Just a note the tour does go rain or shine, and we definitely got caught in the rain towards the end! Our guide, Nora, was a native of Chicago and gave us lots of fascinating history of both food and the city.

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Beth_L, Sept 2026

Amazing and Entertaining Interior Architecture Tour!

Heath was an amazing tour guide! He shared a wealth of information with us about the architecture of the buildings we visited, and he did it in a very entertaining way. I’m so glad my husband and I booked this tour, and I highly recommend it! It was a great value too!

Chicago Favorites Ultimate Food and Walking Tour

Rachel_S, Sept 2026

Amazing!

This was a great experience! Brayden did an amazing job explaining the history of the food and the city itself. He also did a great job keeping us on track. There was more food than is in the description which was a pleasant surprise. It is a lot of walking but it wasn’t bad because of how it was broken up. Probably our favorite excursion while in Chicago…except for seeing the Cubs play.

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

Samara_J, Aug 2026

Interesting and Engaging Walking Tour.

We had so much fun attending this tour. We had a group of 6 and had to reschedule last minute due to very extreme weather. Andre was very kind to let us reschedule for the next day. We loved Andre's presentation and storytelling, and we continued to talk about the things we learned on this tour for the rest of the day. I would highly recommend this tour to anyone interested in learning about the darker side of Chicago history. We were thoroughly entertained! Thank you, Andre!

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

Candace_W, Aug 2026

Just do it!

My family and I did this tour while we were in Chicago this past weekend and we were very happy with our experience. Sue was our guide and she was a wealth of knowledge. You could really tell that she enjoys her job. Before we got started, she made sure that everyone in our group was accounted for and even went out of her way to ensure that a few unintentional latecomers were able to jump in without disruption. She was well-prepared with anything we would've needed like wet wipes, hand sanitizer and even a Tide pen! All of the food options were amazing, with the Lou Malnati's pizza being my favorite dish. I would 100% recommend this tour to anyone visiting Chicago! You'll feel like a local for a few hours. :)

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'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.