img0 img1img2img3img4
Left Arrow
Right Arrow
img1
img2
img3
img4
Rating Star

Viator Rating : 5 (216 reviews)

Dyvarcity Score Icon

Dyvarcity Score : 9.0/10 (Verified Excellent)

Location Icon Chicago

Chicago History Tour: Uncover Downtown's Secrets

Clock

120

Overview

Experience Intelligence

Highlights

Sentiment Analysis

FAQs

Location

Overview

Quotes Logo 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! Quotes Logo

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)

Crowd Density (8 - Empty / Light) : Very few people, free movement

Safety (9 - Secure)

Safety (9 - Secure) : Strong feeling of safety and control

Upsell Risk (10 - Transparent)

Upsell Risk (10 - Transparent) : No upsells or hidden costs

Logistics (8 - Seamless)

Logistics (8 - Seamless) : Smooth and well executed

Mobility (8 - Easy / Accessible)

Mobility (8 - Easy / Accessible) : Comfortable for most people

Pacing (9 - Balanced)

Pacing (9 - Balanced) : Smooth and comfortable timing

Instagram Factor (9 - Iconic)

Instagram Factor (9 - Iconic) : Highly photogenic and memorable

Guide Quality (10 - Exceptional)

Guide Quality (10 - Exceptional) : Engaging and memorable

Guide Reliability (10 - Dependable)

Guide Reliability (10 - Dependable) : On time with strong follow-through

Highlights

Highlight Icon

Discover Chicago's Hidden Stories: Uncover the secrets and fascinating tales behind Chicago's famous landmarks.

Highlight Icon

Explore Iconic Buildings: Go inside amazing buildings and admire the unique architecture of Chicago.

Highlight Icon

Small Group Experience: Enjoy a more personal tour with a small group.

Highlight Icon

All Fees and Taxes Included: No need to worry about extra costs – everything is included in the price.

Sentiment Analysis

  • Positive Highlight Icon Customers loved the guide's knowledge and fun way of telling stories.

  • Positive Highlight Icon Visitors said the tour was interesting and they learned a lot about Chicago's history.

  • Positive Highlight Icon Many people found it to be a great way to see famous places in the city.

  • Positive Highlight Icon The tour is a good mix of history and fun facts.

  • Negative Highlight Icon Some visitors felt the tour could have been shorter.

  • Negative Highlight Icon A few people mentioned it was hard to hear the guide sometimes.

The Journey

1

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.

2

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.

3

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.

4

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.

5

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.

6

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.

7

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.

8

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

From $44 Price

Book Now

As a Viator affiliate partner, we may earn a commission on purchases made through our platform.

Book Now

As a Viator affiliate partner, we may earn a commission on purchases made through our platform.

More like this

Chicago Food, History & Architecture Walking Tour

Location Icon Chicago

$100.95

Chicago Food, History & Architecture Walking Tour

Likely to Sell Out Food & Drink Viator Experience Award 2023

Rating Star 4.9 (1152 reviews)

Duration In Minutes 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.

Details

Book Now

Chicago Food Tour: Bites, History & Secret Dishes!

Location Icon Chicago

$87

Chicago Food Tour: Bites, History & Secret Dishes!

Viator Plus Small Group Low Supplier Cancellation Rate

Rating Star 4.9 (867 reviews)

Duration In Minutes 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).

Details

Book Now

Chicago Art Institute: Skip-the-Line Small Group Tour

Location Icon Chicago

$85.5

Chicago Art Institute: Skip-the-Line Small Group Tour

Historical Tours Museums Low Last Minute Supplier Cancellation Rate

Rating Star 5.0 (152 reviews)

Duration In Minutes 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.

Details

Book Now

Chicago Ghost Tour: Haunts & Hooligans

Location Icon Chicago

$34.77

Chicago Ghost Tour: Haunts & Hooligans

Excellent Quality Historical Tours Low Supplier Cancellation Rate

Rating Star 5.0 (37 reviews)

Duration In Minutes 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.

Details

Book Now

Chicago Insta-Walk: Capture Stunning Photos with a Pro!

Location Icon Chicago

$169

Chicago Insta-Walk: Capture Stunning Photos with a Pro!

Low Last Minute Supplier Cancellation Rate Small Group Excellent Quality

Rating Star 5.0 (31 reviews)

Duration In Minutes 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.

Details

Book Now

Chicago's Hidden Pedway: Underground Walking Adventure

Location Icon Chicago

$65

Chicago's Hidden Pedway: Underground Walking Adventure

Walking Tours Likely to Sell Out Private and Luxury

Rating Star 5.0 (27 reviews)

Duration In Minutes 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.

Details

Book Now

Nearby Events

Labyrinth In Concert: 40th Anniversary at Pabst

Location Icon Pabst Theater

Oct 03

8:00 PM

Labyrinth In Concert: 40th Anniversary at Pabst

Family Miscellaneous Film

Jim Henson's Labyrinth In Concert brings the cult classic film to Pabst Theater in an immersive live experience. Fans watch the 1986 fantasy on a stunning HD screen while a live band performs the full soundtrack in perfect sync with David Bowie’s iconic vocals, celebrating the movie’s 40th anniversary on a global tour hitting over 60 North American cities.

Jim Henson’s Labyrinth, directed by Henson himself and starring Jennifer Connelly and David Bowie as the Goblin King Jareth, captivates with its magical world of fantastical creatures from Henson’s Creature Shop and timeless songs like “Magic Dance.” This fusion of film and live music revives the sweeping score by Bowie and Trevor Jones like never before. The historic Pabst Theater, a Milwaukee landmark, provides an intimate setting for this nostalgic spectacle.

Details

Book Now

Weird Al in Milwaukee: Get Tickets Here!

Location Icon Fiserv Forum

Oct 17

8:00 PM

Weird Al in Milwaukee: Get Tickets Here!

Comedy Arts & Theatre

“Weird Al” Yankovic brings his Bigger & Weirder Tour to Milwaukee's Fiserv Forum, promising an evening of hilarious parodies and original comedic tunes. Having recently starred in the biopic “Weird: The Al Yankovic Story” and continuing to delight audiences with his unique brand of musical humor, Weird Al remains a relevant and beloved figure in comedy. Expect a high-energy performance filled with costume changes, visual gags, and all the accordion-fueled madness fans have come to adore.

Weird Al's career spans decades, marked by iconic parodies and a dedicated fanbase. Fiserv Forum, a state-of-the-art venue in downtown Milwaukee, is known for hosting major concerts and sporting events, ensuring a comfortable and memorable experience for all attendees.

Details

Book Now

Lion King in Concert: Milwaukee Tickets

Location Icon Miller High Life Theatre

Mar 22

12:00 PM

Lion King in Concert: Milwaukee Tickets

Music Film

The Music of The Lion King – Live in Concert brings the iconic Disney soundtrack to life at Miller High Life Theatre with a symphonic orchestra, dynamic percussionists, and soaring choral harmonies from star soloists of the original Broadway productions.
This multisensory tribute features timeless hits like “Circle of Life,” “Hakuna Matata,” and “Can You Feel the Love Tonight,” enhanced by immersive visuals, state-of-the-art lighting, and vibrant projections that capture the majesty of the African savanna. Performed by the Broadway Symphonic Orchestra & Choir, it delivers the emotional depth and cultural richness of the beloved film and musical. Miller High Life Theatre, a historic venue in Milwaukee's Wisconsin Center District, provides an elegant backdrop for this captivating performance.

Details

Book Now

Theresa Caputo Live at Morris Performing Arts Center

Location Icon Morris Performing Arts Center

Jun 17

7:30 PM

Theresa Caputo Live at Morris Performing Arts Center

Hobby/Special Interest Expos Miscellaneous

Theresa Caputo brings her acclaimed live tour to the Morris Performing Arts Center in South Bend, Indiana, offering fans a rare chance to experience her signature blend of spiritual connection and heartfelt storytelling. Known for her hit TV series 'Long Island Medium,' Caputo continues to captivate audiences nationwide with her ability to deliver messages from loved ones, creating an emotional and uplifting evening for all.

Theresa Caputo’s live performances are celebrated for their authenticity and warmth, making each show a unique journey of healing and hope. The Morris Performing Arts Center, a historic venue renowned for its elegant architecture and intimate atmosphere, provides the perfect backdrop for this unforgettable event.

Details

Book Now

Jimmy Failla Live at Coronado Theatre

Location Icon Coronado Theatre

Aug 22

7:30 PM

Jimmy Failla Live at Coronado Theatre

Multimedia Arts & Theatre

Jimmy Failla brings his razor-sharp stand-up comedy to the historic Coronado Theatre in Rockford, IL, delivering his signature humor drawn from his journey as a former New York City cab driver turned Fox News host. Known for his nationally syndicated radio show Fox Across America and hosting Fox News Saturday Night, Failla's performances blend everyman wit with timely takes on politics, pop culture, and everyday absurdities, as showcased in his stand-up special They're Just Jokes on Fox Nation.

Jimmy Failla, a New York Times bestselling author of Cancel Culture Dictionary, captivates audiences with relatable stories from driving cabs in NYC to opining on major Fox News programs like Hannity and Gutfeld. The iconic Coronado Theatre, a 1920s movie palace famed for its Spanish Revival architecture and superb acoustics, provides an intimate backdrop for his high-energy show.

Details

Book Now

Seven Lions Live at Radius Chicago Tickets

Location Icon Radius - Chicago

Apr 04

10:00 PM

Seven Lions Live at Radius Chicago Tickets

Other Music

Seven Lions brings his genre-defying melodic bass sound to Radius - Chicago, fusing trance, dubstep, and mainstream pop in a high-energy electronic dance music performance. California producer Jeff Montalvo, aka Seven Lions, rose to fame after winning a 2012 Beatport remix contest for Above & Beyond's 'You Got to Go,' earning support from Skrillex's OWSLA and releasing chart-topping EPs like Worlds Apart and his debut album Beyond the Veil in 2022.

Seven Lions continues to innovate with his label Ophelia Records, which has amassed over a billion streams, bridging ethereal trance vibes with adrenaline-pumping bass music that has headlined festivals like EDC Las Vegas and Ultra Music Festival. Radius - Chicago offers an intimate club atmosphere perfect for immersive EDM experiences.

Details

Book Now

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