Viator Rating : 5 (216 reviews)
Dyvarcity Score : 9.0/10 (Verified Excellent)
Chicago
Chicago History Tour: Uncover Downtown's Secrets
120
Overview
Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour offers a profound walk through downtown Chicago. It uncovers incredible stories and secrets of the city. This walking tour explores “Da Loop,” peeling back the layers of Chicago to reveal its history and beauty.
Participants can expect an engaging and eye-opening experience. The tour goes inside extraordinary buildings and admires amazing art and architecture, uncovering how it all came to be. Key stops include the Chicago Cultural Center, Chicago Board of Trade Building, Federal Plaza, Reliance Building, Chicago Picasso, Chicago Theatre, and Marshall Field's (Macy's on State Street).
This experience includes all fees and taxes. Expert local guides lead small groups through the city's most iconic landmarks, sharing stories and insights along the way. Get ready to walk and discover the heart of Chicago! 
Experience DNA Fingerprint
Scores are shown on a scale of 1 to 10, 1 = lowest score, 10 = highest score.
What People Love
Crowd Density (8 - Empty / Light) : Very few people, free movement
Safety (9 - Secure) : Strong feeling of safety and control
Upsell Risk (10 - Transparent) : No upsells or hidden costs
Logistics (8 - Seamless) : Smooth and well executed
Mobility (8 - Easy / Accessible) : Comfortable for most people
Pacing (9 - Balanced) : Smooth and comfortable timing
Instagram Factor (9 - Iconic) : Highly photogenic and memorable
Guide Quality (10 - Exceptional) : Engaging and memorable
Guide Reliability (10 - Dependable) : On time with strong follow-through
Highlights
Discover Chicago's Hidden Stories: Uncover the secrets and fascinating tales behind Chicago's famous landmarks.
Explore Iconic Buildings: Go inside amazing buildings and admire the unique architecture of Chicago.
Small Group Experience: Enjoy a more personal tour with a small group.
All Fees and Taxes Included: No need to worry about extra costs – everything is included in the price.
Sentiment Analysis
Customers loved the guide's knowledge and fun way of telling stories.
-
Visitors said the tour was interesting and they learned a lot about Chicago's history.
-
Many people found it to be a great way to see famous places in the city.
-
The tour is a good mix of history and fun facts.
Some visitors felt the tour could have been shorter.
-
A few people mentioned it was hard to hear the guide sometimes.
The Journey
Chicago Cultural Center
Marvel at Marc Chagall's breathtaking 'Four Seasons' mosaic mural within the stunning Chicago Cultural Center. Once Chicago's first central public library, this architectural masterpiece now hosts free cultural events and exhibitions, showcasing the city's commitment to art and community. Explore its opulent Preston Bradley Hall, adorned with a Tiffany glass dome, and discover why it's considered one of Chicago's true gems.
Chicago Board of Trade Building
Behold the Chicago Board of Trade Building, an Art Deco masterpiece that stands as a symbol of Chicago's financial prowess. Observe the building's iconic facade crowned by a statue of Ceres, the Roman goddess of agriculture. Inside, discover the bustling trading floors where billions of dollars change hands daily, and delve into the history of commodity trading that has shaped Chicago's economic landscape.
Federal Plaza
Experience the intersection of Modern Art and Modern Architecture at Federal Plaza. Admire Alexander Calder's vibrant 'Flamingo' sculpture, a bold statement against the backdrop of Mies van der Rohe's minimalist architecture. Reflect on the powerful juxtaposition of art and urban space, and understand how these iconic works contribute to Chicago's unique cultural identity.
Reliance Building
Step back in time at the Reliance Building, one of Chicago's oldest skyscrapers and a pioneering example of the Chicago School of architecture. Admire its large glass windows and innovative steel-frame construction, which revolutionized skyscraper design. Discover the building's history as a symbol of Chicago's architectural innovation and its enduring legacy as a National Historic Landmark.
Chicago Picasso
Stand in awe before the Chicago Picasso, a monumental 50-foot sculpture that Pablo Picasso gifted to the city. Contemplate the abstract form and its enigmatic meaning, sparking dialogue and interpretation among viewers for generations. Discover how this iconic sculpture has become a beloved symbol of Chicago's artistic spirit and a must-see landmark for visitors.
Chicago Theatre
Immerse yourself in the glitz and glamour of the Chicago Theatre, an iconic landmark that has hosted legendary performers for nearly a century. Marvel at its opulent Baroque design, inspired by French palaces, and imagine the countless stars who have graced its stage. Take a tour to learn about the theater's rich history and its enduring role as a cultural beacon in the heart of Chicago.
Marshall Field's (Macy's on State Street)
Delve into the history of Marshall Field's, now Macy's on State Street, a revolutionary department store that once reigned as the largest in the world. Explore its grand architecture, including the iconic Great Clocks and Tiffany glass ceiling. Discover the legacy of Marshall Field, a visionary merchant who transformed the retail experience and shaped Chicago's consumer culture.
Chicago Cultural Center
Explore the Chicago Cultural Center, a magnificent architectural gem that embodies the city's commitment to arts and culture. Originally the city's central library, this landmark boasts stunning interiors, including the world's largest stained-glass Tiffany dome. Discover free exhibitions, concerts, and events held within its walls, and immerse yourself in Chicago's vibrant cultural scene.
Know Before You Go
This walking tour includes all fees and taxes. What is not included is personal expenses. Please meet your guide at the designated meeting point in downtown Chicago. Comfortable shoes are recommended, as this is a walking tour.
Hot Tip
Many visitors suggest wearing comfortable shoes, as there is a lot of walking. Also, try to arrive a few minutes early to find the meeting spot and be ready to start on time!
Review Summary
Reviews on Viator and other public sites consistently praise the Walkin' with Colin tour for its engaging storytelling, entertaining mix of history, comedy, and mystery, and the guide's deep knowledge of Chicago's downtown area. Travelers particularly appreciate the tour’s small group size and insightful stops at notable buildings and art. Some note that the walking pace and outdoor nature might be challenging in hot or humid weather, and the tour is not fully accessible for those needing mobility aids. Overall, it is highly recommended for visitors seeking a captivating, unique perspective on Chicago’s layered history.
This page is synthesized and developed by Dyvarcity Team
More like this
Chicago
$100.95
Chicago Food, History & Architecture Walking Tour
4.9
(1152 reviews)
Duration: 270
minutes
Chicago in a Day: Explore Food, History, and Iconic Architecture. This walking tour takes people through the heart of Chicago, showcasing its food, history, and buildings. It's a tasty way to see the city and learn some fun facts.
Visitors will walk along the Riverwalk, see the Wrigley Building, and snap photos at Millennium Park by Cloud Gate, also known as 'The Bean'. The tour also explores hidden spots like the Chicago Pedway and the bustling energy of Chicago's Main Artery. Expert local guides share stories about Chicago's past, from the Prohibition era to the Great Fire.
This tour includes stops at the Chicago Theatre, City Hall-County Building and the Loop. It includes Chicago's famous eats like deep-dish pizza, a Chicago-style hot dog, and Italian beef. The tour is limited to a small group of 12, making it personal and relaxed. This experience is run by a certified B Corp, which means they care about ethical and responsible tourism.
Chicago
$87
Chicago Food Tour: Bites, History & Secret Dishes!
4.9
(867 reviews)
Duration: 180
minutes
Chicago Walking Food Tour With Secret Food Tours lets one savor the Windy City's vibrant flavors! This isn't just a food tour; it's a delicious journey through Chicago's history and culture, one bite at a time. This walking tour explores the famed Chicago Loop District, showcasing world-renowned architecture and public art. See landmarks like the Harold Washington Library Center, walk along LaSalle Street, admire The Flamingo (Calder Sculpture), and catch a glimpse of the Willis Tower (Sears Tower), The Rookery Building, and the Palmer House Hilton.
What can visitors expect? The tour includes the city's biggest food hits, many with roots dating back over 150 years. Imagine tasting the iconic deep-dish pizza, sinking your teeth into an amazing Italian beef sandwich, munching on gourmet popcorn, and savoring other treats. There's also a mouth-watering secret dish that’s revealed only on the day of the tour! The local guide will provide insights along the way.
The tour includes an Italian Beef Sandwich, a brownie, a Chicago-style Hot Dog, a delicious Secret Dish, Deep Dish Pizza with Sausage, and Gourmet Popcorn. It excludes hotel pickup and drop-off, and gratuities (optional).
Chicago
$85.5
Chicago Art Institute: Skip-the-Line Small Group Tour
5.0
(152 reviews)
Duration: 150
minutes
Skip the Line Art Institute of Chicago Tour Semi-Private 8ppl Max. This tour lets people see amazing art without waiting in long lines. It is a walking tour that is great for people who like art and history.
What to Expect: The Art Institute of Chicago is a very popular museum, just like the Met in New York or the Louvre in Paris. On this 2.5-hour tour, a friendly guide will take a small group (8 people max) to see the most famous artworks. Some of the art you might see includes *Paris Street, Rainy Day*, *Sunday on La Grande Jatte*, and *Nighthawks*. But sometimes, art is not there because it is being fixed or moved.
This tour includes all entrance fees and a guide who knows a lot about art. It does not include tips for the guide or rides to and from your hotel. It's easy to get to the museum by taxi or UBER.
Chicago
$34.77
Chicago Ghost Tour: Haunts & Hooligans
5.0
(37 reviews)
Duration: 90
minutes
The Chicago Haunts and Hooligans Tour explores the spooky side of the Windy City. This walking tour takes people through secret spots and underground tunnels, telling tales of ghostly happenings.
Starting at Harry Caray's Italian Steakhouse, a guide in costume leads the way. Expect to hear stories about Chicago's past, including its famous bootleggers and the ghosts that still wander the city. This tour offers a unique look into Chicago's haunted history. People will explore the creepy past of one of Chicago’s most famous bootleggers, offering glimpses into the past and revealing the stories of long-dead phantoms and specters who still call Chicago home.
The tour includes a local guide to lead the way. Drinks are not included but are available to buy. Tips for the guide are also not included.
Chicago
$169
Chicago Insta-Walk: Capture Stunning Photos with a Pro!
5.0
(31 reviews)
Duration: 60
minutes
The Chicago Insta Walk offers a fun, relaxed exploration of the city, capturing stylish photos with digital and Polaroid cameras. Receive 100 digital photos (10 color-corrected) and 5 Polaroid prints for unique souvenirs. A friendly tour guide helps you discover Chicago from a fresh perspective.
Chicago
$65
Chicago's Hidden Pedway: Underground Walking Adventure
5.0
(27 reviews)
Duration: 180
minutes
Walking Tour: Underground Chicago via the Pedway is an adventure that explores the city's secret underground tunnel system, called the Pedway, and some special sights above ground. This walking tour is perfect for anyone who wants to see a different side of Chicago and learn about its history and culture.
The tour starts in the Swissotel lobby with a short introduction to the Pedway. Guests will go underground to visit the Cultural Center and see the beautiful Tiffany Dome. The tour continues through the Pedway to Macy's, where visitors can admire the Tiffany ceiling and the famous Walnut Room. Then the tour heads west to see the Picasso sculpture in Daley Plaza and the Chicago Temple with its Sky Chapel.
After a quick train ride, the tour arrives at the start of Route 66, where guests can take photos with the Art Institute's lion statues. Finally, the tour visits Millennium Park to see Cloud Gate (The Bean), Lurie Gardens, and Crown Fountain. The tour includes transit tickets and a local expert guide. Gratuities, food, and drinks are not included.
Nearby Events
Illinois Railway Museum
July 11
11:30 AMDay Out with Thomas at Illinois Railway Museum
Day Out With Thomas (TM), Thomas & Friends brings the magical world of Sodor to life at the Illinois Railway Museum in Union, IL. Families board a real 20-minute train ride with the iconic blue engine Thomas the Tank Engine, meet Sir Topham Hatt, and dive into hands-on activities like storytelling, coloring, and playtables, all part of the Let's Rock, Let's Roll Tour featuring music-inspired fun and lawn games.
Thomas & Friends captivates generations with its timeless tales of friendship and adventure on the Island of Sodor, making this event a dream for young train enthusiasts. The Illinois Railway Museum, North America's largest, offers unlimited access to historic locomotives, streetcars, and exhibits, blending fantasy with real railway heritage.
American Family Field
May 08
6:40 PMBrewers vs Yankees Tickets at American Family Field
Milwaukee Brewers vs. New York Yankees lights up American Family Field in an electrifying MLB showdown between two powerhouse teams. This interleague clash promises high-stakes baseball action, with the Brewers defending home turf against the storied Yankees, known for their dynasty of 27 World Series titles and relentless pursuit of another championship.
The Milwaukee Brewers bring National League grit and a passionate fanbase to the diamond, while the New York Yankees embody AL dominance with iconic stars and a legacy of clutch performances. American Family Field captivates with its retractable roof and scenic backdrop.
Soldier Field
Jun 27
5:30 PMEd Sheeran LOOP Tour: Live at Soldier Field Chicago
Ed Sheeran brings his highly anticipated LOOP Tour to Soldier Field in Chicago, delivering an unforgettable evening of pop music and heartfelt storytelling. Known for his chart-topping hits and intimate live performances, Sheeran is set to captivate fans with new music and fan favorites in one of the city’s most iconic venues.
Soldier Field, home of the Chicago Bears and a historic landmark on the shores of Lake Michigan, offers a world-class concert experience with sweeping views and top-tier acoustics. The LOOP Tour marks Sheeran’s first major North American stadium run since his record-breaking Divide Tour, making this a must-see event for music lovers.
House of Blues Chicago
May 27
6:30 PMSam Yo Live at House of Blues Chicago
Sam Yo takes the stage at House of Blues Chicago for an captivating lecture-seminar blending intellectual discourse with unique miscellaneous insights. Known for his thought-provoking presentations, Sam Yo delivers content that challenges perspectives and sparks deep conversations among attendees.
Sam Yo has built a reputation for dynamic talks that explore innovative ideas and real-world applications, drawing crowds eager for knowledge and inspiration. House of Blues Chicago stands out with its vibrant atmosphere and prime River North location, perfect for immersive experiences.
Hard Rock Live Rockford
Aug 07
7:00 PMJo Koy Live at Hard Rock Live Rockford
Jo Koy Live brings the Filipino-American comedy superstar to Hard Rock Live Rockford for an unforgettable night of stand-up laughter. Known for his high-energy storytelling and observational humor drawn from family life and cultural quirks, Jo Koy captivates audiences worldwide with sold-out tours and Netflix specials like 'Live from Seattle' and 'Comin' in Hot'.
Jo Koy's meteoric rise from small clubs to global arenas stems from his relatable routines and impeccable timing, earning him a massive following and Grammy nominations. Hard Rock Live Rockford offers an intimate yet electrifying space perfect for comedy.
The Chicago Theatre
Sep 26
7:00 PMBassem Youssef: The Belly of the Beast Tour
Bassem Youssef: The Belly of the Beast Tour brings the Egyptian-American comedian and satirist to The Chicago Theatre for an evening of sharp political commentary and observational humor. Known globally as the "Egyptian Jon Stewart," Youssef has captivated audiences worldwide with his fearless approach to comedy that blends social critique with intelligent wit. This tour marks his continued expansion into English-language stand-up, where he applies the same uncompromising satirical lens that once drew 40 million weekly viewers to his groundbreaking television show.
Youssef's journey from cardiac surgeon to internationally acclaimed satirist has made him one of the most influential comedians of his generation. His ability to tackle complex political and social issues with humor has earned him recognition as one of Time magazine's 100 most influential people. The Chicago Theatre, one of America's most iconic performance venues, provides the perfect backdrop for an artist who has spent his career challenging authority and sparking meaningful conversation through comedy.
Chicago Best Things to Do: Concerts, Helicopter & Food Tours
The Chicago skyline is hiding a secret- a ton of them, actually. It’s more than a view: it’s got adventures you're meant to explore. Breathe in the winds and excitement of a helicopter tour, party at top concerts, or dive into food and pizza tours. Walk beside history on a gangster mob tour, take a fireboat or bus tour. Looking to get wild tonight? Find events going on sooner than tomorrow, from EDM to country concerts. Check all your bucket list boxes, and live stories you’ll remember forever.
View Chicago Activities