Top Chicago Walking Tours

Chicago Favorites Ultimate Food and 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.

(2,270)

from $85

Chicago Gangsters and Ghosts Walking Tour

Chicago Gangsters and Ghosts Walking Tour

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.

4.8

(140)

from $38

Chicago Architecture Tour: Underground Pedway and the Loop

Chicago Architecture Tour: Underground Pedway and the Loop

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.

(542)

from $35

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

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

(784)

from $80

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.

(390)

from $35

Original Chicago Architecture Interiors Tour: Dazzling Interiors

Original Chicago Architecture Interiors Tour: Dazzling Interiors

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.

(1,773)

from $35

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

(1,352)

from $101

Chicago Walking Tour: Must-See 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.

(162)

from $35

Chicago Walking Tour: Historic Treasures of Chicago

Chicago Walking Tour: Historic Treasures of Chicago

Stroll through Chicago's winter streets, lit up for the holidays, without the hassle of navigating the city yourself on this gourmet walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows on State Street, and ice skating at Millennium Park. Sample generous tastes of classic Chicago foods and holiday treats as you walk.

(440)

from $35

Christkindlmarket Chicago brings festive magic to your Chicago Food Tour, w/ hot cider, twinkling stalls, & the cozy charm of the Chicago Holidays—a perfect spot to savor the season’s warmth & spirit.

Chicago-Style Holiday Hike: Festive Food and Walking Tour

Discover the rich history and architecture of downtown Chicago with local expert Dave Lineal. Walking underneath the soaring buildings, we will learn how Chicago grew to become a global force in culture, commerce, and architecture. How did this roaring city come to be? We will hear the tales of Chicago history immersed in the places where it happened -- exploring historic building interiors like the world's oldest skyscrapers, City Hall, and the old library. This deep dive in city history and architecture aims to deepen our appreciation of what Chicago is today.

(81)

from $85

History and Architecture of Chicago Loop Walking Tour

History and Architecture of Chicago Loop Walking Tour

Explore the new Old Post Office Building, whose early 20th-century design has been adaptively reused into a beautiful, modern Class A Office building. It once seemed as though the stunning architectural details of Chicago's Old Post Office would be lost to time while the building sat vacant for almost two decades. But the 2.8 million square foot building, completed in 1934, recently went through a monumental renovation and now serves as a modern multi-use event and office space that meets today's need for large, light-filled workspaces. See how historic artifacts and building details have been creatively incorporated into the Old Post Office's design including the conversion of the roof to a 3.5-acre urban rooftop park. Old places can become new spaces when a developer with vision collaborates with an award-winning architectural team.

(23)

from $33

Explore the Historic Old Post Office in Chicago

Explore the Historic Old Post Office in Chicago

Discover one of Chicago’s most picturesque, historic neighborhoods—and learn all about the buildings that make it an architectural standout—on this small-group walking tour of Wicker Park. Meet your guide in the morning, and set off on foot: you’ll discover the 19th-century workers’ cottages that fill the neighborhood, will admire local landmarks like mansions and historic baths, and will learn all about the city’s architectural history.

(25)

from $15

Historic Homes and Cottages of Wicker Park Walking Tour

Historic Homes and Cottages of Wicker Park Walking Tour

1 hour 30 minutes

Leave behind Chicago’s buzz and see the Windy City as it used to be, some 150 years ago. The Oldtown Triangle—one of the most beloved ‘hoods in the city—survived the Great Chicago Fire of 1871, and it still stands today as a beacon to history. With your guide at the helm, you’ll witness fantastic architecture, national landmarks, and hear stories of the city’s often wild past.

(48)

from $45

Workers Cottages of Oldtown Triangle Walking Tour

Workers Cottages of Oldtown Triangle Walking Tour

1 hour 45 minutesFree Cancellation

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.

(54)

from $45

Chicago: Gangsters and Food Tasting Walking Tour

Chicago: Gangsters and Food Tasting Walking Tour

This tour is ideal for first-time visitors or anyone eager to discover the city’s most iconic Top Attractions and Highlights on a guided Chicago Walking Tour. During this 2-hour Walking Tour of Chicago, stroll through downtown’s beautiful streets as expert local guides share rich history, colorful characters, and insider tips to enhance your list of Things to do in Chicago. Your experience includes a FREE 2-hour bike or kayak rental—bike the Lakefront Trail or kayak on Lake Michigan for unforgettable skyline views. Bobby’s Bike Hike tours are nationally recognized by National Geographic, USA Today, and Condé Nast Traveler for excellence in storytelling and urban exploration. You’ll see the landmarks that define Chicago: Millennium Park, the Chicago Riverwalk, the Wrigley Building, the Chicago Theatre, and the famed Magnificent Mile. Covering 1.5 miles (2.25 km) of easy, flat terrain, this tour offers a complete and memorable introduction to the city.

4.6

(24)

from $80

Visit Cloud Gate on our Chicago Walking Tour—a Walking Tour of Chicago featuring Top Attractions, iconic art, and unforgettable Highlights at the city’s most photographed landmark.

Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

Leave behind the stuffy, slow-moving tour groups and explore Chicago’s Millennium Park on your own with a private, self-guided app tour. Using just your smartphone, pausing as you like, you’ll learn all about “The Bean,” Lurie Garden, Crown Fountain, and more. With your GPS cuing your audio experience, this tour lets you go at your pace, style, and time, with lifetime access and no expiry.

(6)

from $45

Chicago Millennium Park Self-Guided Walking Tour

Chicago Millennium Park Self-Guided Walking Tour

1 to 2 hoursFree Cancellation

4.6

(5)

from $15

Chicago Architecture and True Crime History Tour

1 hour 30 minutes to 1 hour 45 minutesFree Cancellation

Chicago Crime, Mobsters & Ghosts Walking Tour

(585)

from $35

1 hour 30 minutes to 2 hoursFree Cancellation

4.7

(456)

from $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

(996)

from $85

Haunted Chicago Booze and Boos Ghost Walking Tour

2 hours 30 minutesFree Cancellation

Chicago River 90-Minute Architecture Boat Tour

(322)

from $36

Likely to Sell Out

Explore haunted Chicago at your own pace and schedule. Go anytime. Why take this tour? -It's like an in person tour guide, only it's on your phone. -Tour at your own pace and schedule -Professionally produced, narrated and musically edited immersive experience -Guided by technology. Put your phone in your pocket as the smart phone tour guided you with voice turn by turn. -Great deal -See and learn about Chicago's haunted spots, tragic events, fires, and the spirits that stayed behind. -Listen again after taking the tour. -The tour never expires, go or listen (after the on location tour) anytime. This haunted adventure is a smart phone guided on location tour. You go to the first stop, open the tour, enter your experience code and press play. From there you are guided turn by turn through Huntsville. The app knows your location and seamlessly guides you each step of the way.

4.8

(1,866)

from $37

Chicago Haunted Ghost Tour GPS Self-Guided Walking Tour

Chicago Haunted Ghost Tour GPS Self-Guided Walking Tour

1 hour to 1 hour 15 minutesFree Cancellation

4.8

(5)

from $10

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

Chicago's Chinatown Food and Walking Tour

(224)

from $35

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Jacob_B, Aug 2026

Bringing the roots of China to the city of Chicago

Bring an empty stomach and get ready to indulge in a world of culture and cuisine with a history lesson at every stop! Valarie was the most amazing guide and hosted us with kindness and compassion! She’s fantastic and nothing can go wrong when you’re with her!!!

Chicago Architecture and True Crime History Tour

John_D, Aug 2026

Most Interesting Experience on our Trip!!

This experience made our trip to Chicago a lot more memorable. So many interesting stories that made each place 10x better. Grant was very knowledgeable and super great at telling his stories. Felt something like a Netflix series in real life or a an interactive documentary.

Chicago Architecture Tour: Underground Pedway and the Loop

Amber_P, Aug 2026

This experience was unique, interesting, and informative.

This experience was unique, interesting, and informative. I would never have known these pathways existed and found it fascinating that many locals are unaware of this infrastructure. Our guide is absolutely passionate about architecture and it is apparent he loves his job showing guests this network of paths and pointed out architectural features and innovations I would never have noticed otherwise.

Art Institute of Chicago Skip-the-Line Exclusive Guided Tour

Jodie_B, Aug 2026

Informative, speedy way to view the key pieces.

We know a little about art, so it was helpful to enter the gallery before opening time (you notice the crowds, once it is open to the public) and have Megan guide us to the pictures you should see if on limited time. 2 to 2 1/2 hours is probably the amount of time you need before you decide you have had enough.

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

Terry_W, Aug 2026

Great Tour, well worth the time and money.

Sue is wonderful, born in Chicago so she knows the great food places. All the food was delicious, better than I expected. The pizza was so good, I never eat that kind of pizza but I ate the entire piece. The brownies were scrumptious, even though I was full, there was always room for a great brownie. Sue's knowledge of the Chicago history made the tour an absolute must for anyone who is interested in great facts and stories. I would recommend this tour to all.

Private 45-Minute Chicago Skyline Helicopter Tour

Richard_W, Aug 2026

Our Family day in the sky...

Our Family day in the sky was absolutely perfect! There were a few nerves when we arrived but pilot answered all of our questions and guide us on an unforgettable tour, circling downtown, Navy pier, the Stadiums, Chicago River - it was incredible. If you are thinking about it, just do it! It’ll be a memory that will last a lifetime.

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

Chris_C, Aug 2026

Ghosts, Fires, and Capone

Andre, our tour guide made our tour so fun!! He knows his Chicago History and has so much energy and humor. He is funny, engaging, theatrical, thoughtful, and fun!! Well done Andre!! The tour takes you through macabre Chicago history, and you see the actual locations of the incidents. Interesting and informative… I recommend the tour, and ask for Andre.

Chicago City Minibus Tour

Milady_C, Jul 2026

I ❤️ Chicago

The Chicago Mini Bus Tour was excellent and the driver/guide Rick was so funny and nice. Rick gave us a lot of great recommendations and tips on visiting the city, as well as interesting historic background and fun facts! I highly recommend this tour if you want to see the city highlights in a comfortable bus and take great photos at the popular locations!

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!