Top Chicago Walking Tours

Chicago Favorites Ultimate Food and Walking Tour

3 hoursFree Cancellation

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.

(2,086)

from $85

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

(1,235)

from $101

Original Chicago Architecture Interiors Tour: Dazzling Interiors

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

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

(1,628)

from $35

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

4.8

(16,114)

from $39

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.

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.

Chicago's Chinatown 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.

(677)

from $80

Chicago Architecture Tour: Underground Pedway and the Loop

Chicago Architecture Tour: Underground Pedway and the Loop

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

(473)

from $35

Chicago Walking Tour: Must-See Chicago

(192)

from $35

(148)

from $35

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.

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

(3,207)

from $28

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.

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.

Chicago Walking Tour of Highlights with Free Bike or Kayak Rental

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.

(6)

from $45

Chicago Walking Tour: Historic Treasures of Chicago

Chicago Walking Tour: Historic Treasures of Chicago

(428)

from $35

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.

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

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

Chicago Architecture and True Crime History Tour

(203)

from $40

1 hour 30 minutes to 1 hour 45 minutesFree 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.

(389)

from $35

Chicago Walking Tour: A Walk Through Time

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.

(216)

from $35

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

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

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.

(229)

from $44

Taste of Chicago's Chinatown Food Tours

3 hoursFree Cancellation

Chicago City Private Tours

(2)

from $85

2 to 8 hoursFree Cancellation

4.7

(28)

from $199

Per group

Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour

Chicago dogs, deep-dish pizza, brownies, and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following your guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and the Lakefront Trail. As you go, stop for generous food and beer tasters.

(47)

from $35

From deep-dish to hot dogs, taste Chicago Classic Dishes on our Chicago Food & Bike Tour. Ride by Bicycle, learn the stories, and savor every stop on the best Food & Bike Tour in Chicago.

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

4 hours 30 minutesFree Cancellation

Explore one of the country’s great art museums—and discover many of its collection highlights—on this small-group Art Institute of Chicago tour. Meet your guide right out front, and see works from artists the likes of Picasso, Chagall, Seurat, O’Keeffe, and many more. As you go, your guide will share the stories behind the masterpieces, and will help bring the history of the museum and its collection to life.

(739)

from $89

Skip the Line Art Institute of Chicago Tour Semi-Private 8ppl Max

Skip the Line Art Institute of Chicago Tour Semi-Private 8ppl Max

2 hours 30 minutesFree Cancellation

Price varies by group size

(177)

from $90

Chicago Walking Tour: Art Deco Skyscrapers Loop

Admire the ornamental facades and intricate interiors of the Windy City's art deco buildings during this in-depth walking tour of the vibrant Loop. This small-group tour will introduce you to some of the city's highlight architectural landmarks and its rich history, all in a single excursion. As you go, get an up-close look at landmarks that many other tours overlook—and learn insider stories from your architecture-expert guide.

Chicago Walking Tour: Art Deco Skyscrapers Loop

Chicago Crime and Mob Bus Tour

4.8

(182)

from $35

Special Offer

1 hour 30 minutes to 2 hoursFree Cancellation

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

Chicago River 90-Minute Architecture Tour

Chicago River 90-Minute Architecture Tour

4.7

(10,024)

from $45

Skip navigating around the city with a map and guidebook and explore Chicago's iconic landmarks in just a few hours on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore Downtown and North Side neighborhoods, stopping to visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.

Chicago City Tour with Architecture River Cruise Option

Chicago City Tour with Architecture River Cruise Option

2 to 4 hoursFree Cancellation

4.8

(720)

from $50

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Top Attractions in Chicago

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What are people saying about Chicago

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

FlintPolo_F, May 2026

A new perspective on visuals

This tour made our experience so much more. Spiro was an exceptional guide. He gave us a new perspective why art was being created and the intention of why is a displayed. This tour was enlightening. We learned so much and it open out minds to view art differently. I highly recommend.

Chicago's Chinatown Food and Walking Tour

Lorena_H, May 2026

Chinatown Chicago

We did this on a windy, rainy Sunday when we were in Chicago. It was fabulous! Our target guy’s name was Alex, and he was delightful. He was very knowledgeable and timed everything so that we didn’t spend a lot of time out in the bad weather. There was a ton of food and it was delicious. I would recommend this tour and this guide

Chicago Architecture Tour: Underground Pedway and the Loop

Marcellus_C, Apr 2026

Excellent tour with a lot of learning!

This was an excellent activity that gave us a history of the underground walkway, in addition to some of the historical buildings in Chicago. Henry was very knowledgeable--he was able to answer 95% of our questions (some of our questions did come out of left field!). Keep in mind - the tour starts across the street from City Hall and ends elsewhere. It wasn't a strenuous walk at all (one of us had knee issues--he didn't complain at all.) About the only "climbing" we did was on stairs exiting the underground pedway. Henry also gave us plenty of opportunities for bathroom breaks. My only regret was not eating a good breakfast before taking the 2+ hour walk. (P.s. Henry was an excellent guide for this because of his background in architectural/structural engineering.). I would take this tour again!

Delicious Donuts & City Sights: Chicago's Original Donut Tour

Kimberly_K, Apr 2026

Book this tour!

BOOK THIS TOUR!! My sister and I had a couple of hours before we left Chicago and booked this walking donut tour. We had an absolute blast!! Jackson was a great tour guide. The donuts were absolutely delicious and plentiful. You won't go away hungry. The walking tour was insightful and interesting. One of our favorite adventures of the weekend.

Chicago City Minibus Tour

Nick_B, Apr 2026

We had an incredible...

We had an incredible experience with See It All Chicago, and a big part of that was our tour guide, Rick Rez. Rick was outstanding—knowledgeable, engaging, and full of energy from start to finish. He brought Chicago’s history to life with great storytelling, fun facts, and insights you wouldn’t get just walking around on your own. You can tell he genuinely loves what he does, and that passion made the entire experience even better. The tour was well-paced, informative, and covered both iconic landmarks and hidden gems. Whether you’re visiting Chicago for the first time or you’ve lived here for years, this is absolutely worth it. We highly recommend booking a tour—and if you can, ask for Rick. You won’t be disappointed.

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

Carol_C, Apr 2026

What are you waiting for? BOOK This TOUR!!

We had a great time! My son (17) and I are true crime and ghost junkies and Andre’s tour did not disappoint. He is an amazing storyteller and guide. Great information along with a true insight to the city. Walking was the way to go. We both would highly recommend the tour. 90 min, easy walking and it flew by all ages would enjoy. Why are you still reading this review… you should be booking your tour!🤩

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

Barbara_G, Dec 2025

Spend a few hours...

Spend a few hours learning about Chicago history, architecture and food! We walked around the Loop, filled our stomachs with sweet and savory, and enjoyed learning about the city. Our tour guide, Mike, was knowledgeable, friendly, and funny. Would definitely recommend this tour!

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

Aleksandra_J, Dec 2025

I had such a wonderful...

I had such a wonderful time! I went with my boyfriend and we were lucky enough to get a great tour guide such as Joe! We had a great experience with Joe, he was very knowledgeable and fun to be around! Definitely recommend 💯 %! We saw all sights such as the Chicago Bears stadium, and tried amazing foods such as the worlds famous Chicago hot dog and amazing deep dish pizza like no other! Definitely recommend, try it out you will have fun and learn alot in this tour!

Haunted Chicago Booze and Boos Ghost Walking Tour

Marissa_B, Dec 2025

SO worth it!

Our tour guide was amazing! She felt like a friend just hanging out telling stories with us. She was an amazing storyteller and had a wonderful personality. Highly recommend! I felt like I learned so much. It was one of those hidden gem things to do that didnt feel touristy. The tour made me feel connected in a way to chicago. Very cool experience.