Walkin’ with Colin: Chicago Tour du Jour

Walkin’ with Colin: Chicago Tour du Jour offers an engaging and authentic way to explore the Windy City’s heart in just two hours. For $44 per person, you’ll join a small group led by a knowledgeable guide, Colin, who brings Chicago’s stories to life through vivid storytelling and keen local insights. Starting at the 1 North Dearborn Building, this tour takes you around Chicago’s most notable landmarks, public art, and lesser-known curiosities—all within a manageable, lively walk.

What makes this experience stand out? First, Colin’s enthusiasm and deep knowledge help turn ordinary sights into captivating stories of courage, tragedy, and triumph. Second, the tour’s focus on art and architecture—from Picasso to Calder—gives a layered understanding of Chicago’s visual culture. The two-hour duration makes it a perfect fit for travelers looking for a rich, no-fuss introduction to downtown Chicago, especially those curious about hidden gems and local favorites. One thing to consider: it’s not ideal for children under 13 or travelers with low fitness levels, given the walking pace.

This tour is well-suited for history buffs, art lovers, and anyone wanting a personalized, insider’s perspective on Chicago’s iconic and quirky side. If you enjoy lively storytelling combined with spectacular city views and fascinating buildings, this will likely be a highlight of your visit.

Key Points

• Expert guide: Colin’s enthusiasm and rich stories make the tour both fun and informative.
• Cultural focus: Art, architecture, history, and local oddities are woven into a compelling narrative.
• Inclusive experience: All building entries are included, saving you time and hassle.
• Short and sweet: A two-hour walk deep enough to satisfy curiosity but manageable for most schedules.
• Small group setting: Limited to ten participants, ensuring personalized attention and better interaction.
• Accessible: Wheelchair accessible, suitable for a broad range of visitors.

You can check availability for your dates here:

Exploring Chicago on Foot with Walkin’ with Colin

When you think of Chicago, images of towering skyscrapers, vibrant arts, and a lively waterfront probably come to mind. Yet, experiencing the city through the lens of a passionate local like Colin transforms this from a typical sightseeing route into a genuinely memorable adventure. For just $44, this 2-hour walking tour offers a compact, yet thorough glimpse into Chicago’s bustling downtown, often called “Da Loop,” where history, art, and modern life intersect.

What to Expect and Why It Works

Starting from the Red “1” Roof Entrance of the 1 North Dearborn Building, Colin kicks things off with a friendly, welcoming attitude. You’ll quickly notice his knack for storytelling, which makes even the most familiar sights fascinating. As you stroll, you’ll venture from Millennium Park to the Chicago River, uncovering stunning buildings and art pieces along the way. Expect to see works by Pablo Picasso, Marc Chagall, Alexander Calder, and Jean DeBuffet—artists whose works adorn Chicago’s public spaces, adding an artistic flair to this urban landscape.

One of the tour’s strengths is Colin’s focus on both the celebrated and overlooked sights. Sure, you’ll get photos of iconic landmarks, but you’ll also hear stories about courageous feats, curious calamities, and local secrets. This approach gives you a more authentic feel for Chicago’s character and helps you appreciate the city beyond tourist clichés.

The Art and Architecture You’ll Encounter

Chicago’s architecture is world-famous, and Colin makes sure you see some of its best examples—both inside and outside buildings. From the spectacular views inside certain structures to the spectacular exteriors, you’ll absorb the city’s innovative design. The tour’s emphasis on public art offers a colorful touchpoint, with sculptures and mosaics by renowned artists enriching your understanding of Chicago’s cultural fabric.

Authentic Stories and Local Flavor

Rosina from Germany, one of the recent travelers, noted, “We really enjoyed the tour with Colin. He shared some great info about different buildings, mosaics, and works of art!” It’s clear that Colin’s passion shines through in his ability to weave stories that entertain and inform. His enthusiasm ensures that even those without prior knowledge of Chicago’s history leave feeling like they’ve gained a new appreciation.

A Perfect Fit for Curious Travelers

This tour particularly suits those who love learning on the go—whether history buffs, art lovers, or just curious explorers. Because it’s a small group (limited to 10), you get personal attention, and Colin can adapt to your interests. The inclusion of all building entries is a real bonus, as it avoids unnecessary delays and makes the experience feel more seamless.

The Breakdown of the Itinerary

While the tour isn’t overly detailed in schedule, here’s what you might expect during your walk:

Start Point at Dearborn Building: Colin welcomes you here, giving a quick overview before setting off into downtown Chicago. You’ll be immediately immersed in the city’s lively atmosphere, with views of Millennium Park and the Chicago River.

Millennium Park and Surroundings: You’ll likely pass by famous landmarks like the Cloud Gate (The Bean) and enjoy stories about the park’s design and history. Colin may share anecdotes about the sculptures and public art, including pieces by Picasso and Chagall—highlighting how art shapes Chicago’s identity.

Chicago’s Architectural Gems: The guide takes you in and out of buildings—many with intriguing histories or unique features—highlighting Chicago’s reputation as a leader in skyscraper design. Expect to see spectacular buildings both outside and, where included, inside, with commentary about their architects and innovations.

The Chicago River and Cultural Oddities: Moving toward the river, you’ll learn about Chicago’s remarkable engineering feats, as well as stories of calamities and courageous moments that shaped the city’s skyline.

Hidden and Local Gems: The tour also emphasizes lesser-known spots—places that locals love but travelers often miss—giving you a more authentic feel for the city’s vibrant neighborhoods.

End Point and Final Stories: As you wrap up, Colin might share recommendations for your next Chicago experience, be it visiting museums, dining spots, or other attractions.

The Value of This Tour

For the price, this tour offers excellent value. You’re getting a 2-hour walking experience with a professional guide whose enthusiasm turns sightseeing into storytelling. All building entries included means there are no surprise costs, making it easier to budget your day. The small group size ensures interaction and flexibility—if you’re interested in a particular topic or building, Colin’s probably happy to chat more.

While it’s not an exhaustive historical deep dive, it strikes a balance between entertainment and education. It’s perfect for travelers who want a broad overview without the fatigue of longer, bus-based tours or visits that only scratch the surface. The tour’s focus on visual art, architecture, and local secrets offers a layered appreciation of Chicago’s soul.

Who Should Consider This Tour?

This experience is ideal for travelers who enjoy storytelling and want to see Chicago through a more personal lens. If you appreciate art, architecture, and vibrant city views, you’ll find plenty to love. It’s especially suited for those who prefer walking tours over bus rides, enjoy small group settings, and want to avoid overly commercialized experiences.

Because the tour is not recommended for children under 13 or those with limited mobility, it’s best for active, curious adults or older teens. The 2-hour length makes it accessible for most schedules, whether you’re fitting it into a morning or afternoon.

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FAQs

How long is the tour?
It lasts approximately 2 hours, making it a manageable but thorough introduction to downtown Chicago.

Where does the tour start?
Meet your guide under the Red “1” Roof Entrance of the 1 North Dearborn Building, between Washington and Madison Streets.

What is included in the price?
All building entries are included, and you’ll benefit from a professional, friendly guide throughout the walk.

Is the tour wheelchair accessible?
Yes, it is wheelchair accessible, suitable for a variety of mobility needs.

What should I bring?
Comfortable walking shoes, a water bottle, and perhaps a hat or sunglasses if sunny. The tour runs rain or shine, so dress accordingly.

Can I cancel if my plans change?
Yes, full refunds are available if you cancel up to 24 hours in advance.

Is this tour suitable for kids?
It’s not recommended for children under 13, mainly because of the walking involved and the nature of the storytelling.

Are there multiple start times?
Yes, the tour is usually available in the morning and afternoon, providing flexibility.

How many people typically join?
Small groups are limited to 10 participants, ensuring a more personalized experience.

Final Thoughts

Walkin’ with Colin’s Chicago Tour du Jour offers a lively, engaging way to experience the city’s core. With a focus on art, architecture, stories, and local secrets, it’s perfect for travelers who want a more authentic and immersive feel of Chicago in a short period. Colin’s enthusiastic storytelling makes history come alive, turning a simple walk into a memorable journey through the city’s past and present.

If you value expert guidance, beautiful views, and insider knowledge—and don’t mind a bit of walking—this tour delivers excellent value. It’s especially suited for those who enjoy being active, curious explorers eager to uncover Chicago’s lesser-known treasures along with its celebrated icons.

Whether you’re visiting Chicago for the first time or returning for a deeper appreciation of its vibrant streets, this tour provides a smart, memorable introduction that will leave you with a richer understanding of the city’s character and charm.

You can check availability for your dates here: