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

If you’re visiting Chicago and craving a tour that offers more than just the usual landmarks, Walkin’ with Colin promises to deliver a lively, informative exploration of downtown Chicago’s art, architecture, and intriguing stories. This small-group walking experience has earned perfect ratings and glowing reviews—highlighting the engaging storytelling, stunning sights, and insider knowledge that make it a truly valuable choice for curious travelers.

What we love about this tour is how it balances beautiful buildings, fascinating history, and a dash of humor. Plus, the fact that it’s only about two hours long makes it a perfect way to spend a morning or afternoon — without feeling rushed or overwhelmed. And at just $33 per person, it’s hard to find a more engaging and educational experience for the price. A potential caveat? The tour involves some outdoor walking and stairs, so it’s best suited for those with moderate physical mobility.

This experience is ideal for visitors who want to see Chicago through a local’s eyes, uncover hidden gems, and enjoy a fun, storytelling-led approach. Whether you’re a first-time visitor or a seasoned local, this tour offers fresh insights and a chance to see your favorite city in a new light.

Key Points

• Expert Guide: Colin’s storytelling keeps the tour lively, entertaining, and packed with fascinating facts.
• Architectural Highlights: Discover iconic structures like the Marquette Building and the Chicago Theatre, along with lesser-known marvels.
• Artistic Treasures: See murals and sculptures, including Chagall’s Four Seasons mosaic and Picasso’s 50-foot sculpture.
• Indoor & Outdoor Stops: Experience both exterior sights and inside visits of historic buildings, making the tour weather-proof and engaging.
• Flexible Scheduling & Group Size: Choose between morning or afternoon, with a small group of up to 10 travelers that encourages interaction.
• Great Value: At $33, this tour offers more than just sightseeing—it’s a memorable, educational experience that pays off.

An In-Depth Look at the Tour Experience

The Introduction Point & First Impressions

Starting at 1 N Dearborn St, the tour kicks off with a warm welcome from Colin, whose passion for Chicago’s architecture and history shines through immediately. One reviewer praised his engaging storytelling, noting that within ten minutes, they felt like friends rather than strangers. This personal touch helps set a relaxed, friendly atmosphere for the entire walk.

The First Stops: Art & Architecture

The first highlight is Marc Chagall’s Four Seasons mosaic mural. We loved how Colin explained the significance of this colorful piece, which transforms a building’s façade into a piece of art that’s both stunning and meaningful. Reviewers mention how these visual gems invite you to see the city’s art in a completely new way, beyond typical tourist spots.

Next, the Marquette Building impresses with its grand exterior and beautifully preserved interior. Colin’s insights reveal its importance as one of Chicago’s oldest skyscrapers and one of the city’s architectural masterpieces. Several travelers appreciated the chance to go inside this building—something many tours overlook—adding a layer of intimacy and discovery.

Modern Art & Unique Structures

The tour then moves to Calders Flamingo—a playful juxtaposition of modern art and architecture. Created by Alexander Calder, this sculpture adds a splash of whimsy amidst Chicago’s historic buildings. The Bellamy-style architecture of the Mies van der Rohe-designed Flamingo makes for a striking photo opportunity, especially appreciated by those who love contemporary design.

Picasso’s “Untitled” sculpture is a true centerpiece, standing 50 feet tall. Visitors loved the chance to view this famous piece up close, with many commenting that it felt like a gift from the artist to the city. The sculpture’s grandeur and Colin’s stories about Picasso’s influence in Chicago keep the experience memorable.

The Quirky & Historic

The James R. Thompson Center offers something a little more unusual. With its bold architectural style, the building’s transformation behind the scenes was a highlight for many. Reviewers noted that Colin’s explanation of its history and renovation made it much more interesting than a casual glance.

The Chicago Theatre stops are a favorite for many. Colin shares stories of legendary performers and the theatre’s cultural significance. Though the ticket itself isn’t included, this stop brings the theater’s history vividly to life, making it feel like a personal connection to Chicago’s entertainment scene.

Inside the Iconic Department Store

A visit to Macy’s on State Street takes you into the historic Marshall Field’s. Travelers praised this part of the tour for its inside look at the original department store’s architecture and innovations, such as the revolutionary approach to shopping. It’s an opportunity to see the roots of Chicago’s retail history and appreciate the city’s role in shaping modern department stores.

Cultural & Historic Insights

The Chicago Cultural Center caps the tour, showcasing its stunning architecture and cultural significance. Visitors have loved exploring the building’s interior and understanding its legacy as a public library and cultural hub. Many reviewers mention that Colin’s stories made each stop deeply personal and memorable.

Timing & Group Size

The tour lasts approximately two hours, covering about two miles. The small group size (max 10 travelers) ensures plenty of interaction and personalized attention. Travelers can choose between morning and afternoon sessions, providing flexibility for different schedules.

What Reviewers Are Saying

Reviews consistently praise Colin’s knowledgeability, humor, and storytelling. One reviewer emphasized how Colin “broke up the walk enough so you’re not walking long distances” and “made the experience fun and engaging.” Others mentioned that he took them inside buildings they wouldn’t have entered on their own, turning a typical sightseeing walk into an immersive experience.

Many shared that Colin’s enthusiasm made Chicago’s architecture and art come alive in ways they hadn’t appreciated before. One said, “He helps you see Chicago in a way even the locals don’t,” highlighting how this tour offers fresh perspectives even for those familiar with the city.

The Value for Money

At $33 per person, the tour offers tremendous value. The insider access, beautiful sights, and Colin’s engaging narration mean you’re getting much more than a simple walk. Several reviews mention that the experience exceeded expectations, especially given the cost.

Practical Tips

• Wear comfortable shoes and be prepared for some outdoor walking and stairs.
• The tour is suitable for those with moderate physical activity levels.
• Use public transportation to arrive easily at the meeting point.
• Bring a camera—many stops offer Instagram-worthy views and sculptures.
• Arrive a few minutes early to settle in and get the full experience.

Who Is This Tour Best For?

This tour is perfect for art lovers, architecture buffs, and history enthusiasts looking for an engaging, off-the-beaten-path experience in Chicago. It’s also ideal for those who enjoy storytelling and want to uncover secrets behind the city’s most iconic buildings. Families, couples, or solo travelers will all find it a rewarding way to connect with Chicago’s soul without the hassle of large group tours.

If you’re visiting during cool or unpredictable weather, the mix of outdoor and indoor stops keeps things comfortable. Plus, the small group size fosters a more personal experience, making it perfect for those who want a guided tour that feels more like exploring with a knowledgeable friend.

FAQs

How long is the tour?
It runs for about 2 hours, covering approximately 2 miles of walking, with a mix of outdoor and inside visits.

What is the group size?
The tour is limited to a maximum of 10 travelers, ensuring a more personalized and interactive experience.

What should I wear?
Comfortable walking shoes are recommended, as the tour involves some outdoor walking and stairs. Dress for the weather, and bring an umbrella if rain is forecasted.

Is this tour suitable for all ages?
Yes, the tour is suitable for most moderate physical fitness levels. It’s especially great for adults, families, and seniors who enjoy walking and exploring.

Can I cancel if my plans change?
Yes, free cancellation is offered if you cancel at least 24 hours in advance. Cancellations within 24 hours are not refundable.

Are the stops indoors or outdoors?
A mix—some stops like the Marquette Building and Cultural Center are inside, while others, like Picasso’s sculpture and the Chicago Theatre, are outside.

Final Thoughts

Walkin’ with Colin offers a well-rounded, engaging glimpse into Chicago’s architectural, artistic, and cultural landscape. It’s a standout choice for travelers who want to go beyond the usual tourist spots and experience the city through a storyteller’s eyes. The combination of stunning sights, insider tales, and a manageable pace makes this tour excellent value for money.

Whether you’re a first-timer eager to learn or a local looking to see familiar sights from a fresh perspective, Colin’s tour promises a memorable journey through Chicago’s hidden stories and beautiful facades. If you love exploring cities with a knowledgeable guide who can turn history into stories, this experience is a perfect pick.

In short, this tour is best suited for those curious about Chicago’s architecture and art, seeking a friendly, informative walk that’s both fun and insightful. It’s a fantastic way to spend a couple of hours, leave with new perspectives, and perhaps even come away with a few new pictures to share.

Note: For more information or to book, visit the official listing.