Top Chicago Walking Tours

Chicago Favorites Ultimate 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.

4.8

(2,099)

from USD 85

Total Chicago: From Architecture to Food

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

4 hours 30 minutesFree Cancellation

(1,240)

from USD 101

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

(1,640)

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

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.

(680)

from USD 80

Chicago Architecture Tour: Underground Pedway and the Loop

Chicago Architecture Tour: Underground Pedway and the Loop

(475)

Chicago Walking Tour: Must-See Chicago

1 hour 30 minutesFree Cancellation

(148)

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

1 hour 30 minutesFree Cancellation

(203)

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.

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

4.8

(16,151)

from USD 39

Special Offer

Chicago Scavenger Hunt & Self-Guided Audio Walking Tour

The Best Way to Discover Chicago: Scavenger Hunt & Self-Guided Tour. Play, learn, and walk! Explore at your own pace with a 100% self-guided activity. Start anytime (24/7) with no guides or schedules. Pause for a photo at Maggie Daley Park or a visit to the Shedd Aquarium and resume whenever you're ready—even the next day. This unique team-building activity is perfect for couples, families, and groups. The "Complete City" Package - Everything you need in one app: Interactive Game: Solve puzzles and discover 10+ major attractions, plus hidden gems revealed along the way. Audio & Text: Listen to our audio guide or read the history/legends of each site. Insider Tips: Access hand-picked local restaurant and shop recommendations. What you will visit: Navy Pier, Franklin Delano Roosevelt Bridge, Maggie Daley Park, Millennium Park, The Art Institute of Chicago, Clarence F. Buckingham Memorial Fountain, Queen’s Landing, Field Museum, Shedd Aquarium, and Adler Planetarium.

Chicago Scavenger Hunt & Self-Guided Audio Walking Tour

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 Walking Tour: Historic Treasures of Chicago

(429)

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

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

(918)

from USD 85

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

1 hour 30 minutesFree Cancellation

(217)

Chicago Mobs and Haunts Walking Tour

1 hour 30 minutes to 2 hoursFree Cancellation

4.7

(418)

from USD 34

Discover Chicago like never before with complete freedom to explore at your own rhythm, lingering at fascinating locations or moving swiftly through others as your interests guide you. Our expertly crafted audio experience unveils exclusive historical insights and hidden stories that even longtime residents don't know, transforming you from tourist to insider as you uncover the authentic soul of the Windy City. Unlike rigid group tours that rush you past remarkable details, you'll have the flexibility to choose which attractions captivate you most, creating a personalized journey that matches your curiosity and schedule perfectly. You'll experience the city as locals do – unhurried, authentic, and deeply connected to the stories that shaped this magnificent metropolis, all while enjoying a superior experience that combines the convenience of independence with the depth of expert knowledge.

Chicago Self-Guided Audio Tour

3 to 9 hours

3.9

(9)

from USD 6

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

(3,225)

from USD 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

(6)

from USD 45

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

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.

(203)

from USD 40

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

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

(230)

from USD 44

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 USD 50

Chicago Architecture and True Crime History Tour

1 hour 30 minutes to 1 hour 45 minutesFree Cancellation

(398)

The Art Institute of Chicago houses one of the finest American and Impressionist painting collections in the world, but it can be overwhelming to explore on your own. Remove the guesswork and maximize your time inside the museum on a private tour that covers major highlights by Picasso, Chagall, Warhol, Hopper, and others. Plus, there's no waiting to get inside, as the tour includes a skip-the-line ticket.

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

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

2 hours 30 minutesFree Cancellation

(297)

from USD 90

Skip the hassle of planning your Chicago itinerary with this convenient hop-on hop-off tour, covering the city's must-see sights. With multiple strategically located stops, explore the Windy City at your own pace, hopping off to visit top attractions like the iconic Art Institute and famous skyscrapers. Enjoy insightful audio commentary as you cruise through the city, learning about its rich history and vibrant culture. Perfect for first-time visitors or those short on time, this tour offers flexibility and ease, ensuring you don’t miss any of Chicago’s highlights. Book your ticket today and experience the best of Chicago hassle-free!

Chicago Hop-On Hop-Off Sightseeing Tour by Open-top Bus

Chicago Hop-On Hop-Off Sightseeing Tour by Open-top Bus

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

3.9

(2,256)

from USD 49

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

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

2 hours to 2 hours 30 minutesFree Cancellation

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

(4)

from USD 10

Guide discussing A Sunday on La Grande Jatte

2 hours 30 minutesFree Cancellation

Haunted Chicago: Crime, Ghosts, and Capone Walking Tour

(505)

from USD 84

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Braxton_K, May 2026

Book The Tour! Its Great!

Such a fun experience and honestly one of the highlights of our Chicago trip. Braeden was an amazing tour guide and had the perfect personality for a ghost and crime tour. He was funny, energetic, super knowledgeable, and kept the whole group entertained the entire time. You could tell he genuinely loves Chicago history, and he had a great way of blending the spooky stories, true crime, and historical details together without it ever feeling boring or cheesy. The pacing of the tour was great, the stops were really interesting, and walking through the city at night made the whole experience even better. It felt less like a scripted tour and more like hearing wild Chicago stories from a friend who knows everything about the city. We learned a ton, laughed a lot, and honestly didn’t want the tour to end. Highly recommend this tour if you want something different to do in Chicago, and if you get Braeden as your guide, you’re in for a great night.

Original Chicago Architecture Interiors Tour: Dazzling Interiors

C_J, May 2026

Adam

Our guide, Adam, was absolutely phenomenal. His passion for Chicago’s history and architecture is great, and he kept everyone engaged from start to finish. He didn't just rattle off about facts and odd/new world literature; but he told incredible stories about the buildings and the people who shaped them. I was impressed he knew. Adam is knowledgeable, engaging, and well-paced. If you’re taking a Chicago architecture tour, do yourself a favor and ask for Adam. Truly an unforgettable experience!

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

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.

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 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!

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!

Chicago Walking Tour: Historic Treasures of Chicago

Krista_G, Nov 2025

Pleasant walking tour to see 10 historic Chicago buildings.

Very pleasant walking tour led by our knowledgeable guide, Burt, who showed us 10 historic buildings in downtown Chicago, starting with the Wrigley building on down to the Palmer Hotel. The weather was great, so the streets were crowded and very noisy, but hey, this is Chicago! We saw lots of historic interiors as well. Well worth the time and cost of the ticket.