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

Thinking about taking a walking tour in downtown Chicago? We’ve come across Walkin’ with Colin and its highly-rated History-Mystery-Comedy-Tragedy Tour, and it’s worth sharing what makes it stand out—and what to consider before booking. This tour promises a two-hour journey through Chicago’s streets filled with stories, art, and fascinating buildings, all guided by a charismatic local.

What really caught our attention are the personalized storytelling style and the chance to see inside some of the city’s iconic buildings—all for just $33 per person. And with a perfect 5.0 rating from over 125 reviews, it’s clear that many find it both enjoyable and informative. The fact that it’s designed for small groups (max 10 people) also makes it feel intimate and tailored.

But, as with any tour that involves walking outdoors and some indoor exploration, weather and physical stamina matter. If you’re not comfortable with a moderate amount of walking or standing, or if the forecast calls for rain, it’s good to plan accordingly. This tour is best suited for those who love a mix of history, architecture, and a touch of humor—perfect for curious travelers eager to see Chicago beyond the usual tourist spots.

Whether you’re new to the city or a seasoned local, this tour offers hidden gems and inside looks at Chicago’s buildings and stories, making it especially appealing for art lovers, architecture buffs, and history enthusiasts.

Key Points

• Highly rated guide: Colin’s storytelling style garners glowing reviews, making all the difference.
• Indoor and outdoor stops: You’ll visit both exterior landmarks and explore inside historic buildings.
• Affordable price: At $33, it’s a good value for a personalized two-hour experience.
• Flexible scheduling: Morning and afternoon options allow for convenient planning.
• Small group size: Limited to 10 travelers, ensuring a more engaging and personalized experience.
• Diverse highlights: From art like Picasso’s sculpture to historic department stores, the tour balances visual treats with engaging stories.

Exploring the Tour’s Itinerary

Start at Chagall’s Four Seasons Mosaic

Right from the beginning, the tour kicks off with a vivid visual—Marc Chagall’s stunning mosaic mural. It’s a perfect way to set the tone: art that’s both colorful and meaningful. As you stand before this masterpiece, your guide will probably share insights into the artist’s influence and the significance of this work in Chicago’s landscape. Expect a quick 15-minute stop, during which you’ll get a glimpse of the city’s artistic side without it feeling rushed.

Marquette Building: A Glimpse into Chicago’s Architectural Past

Next, you’ll visit one of Chicago’s oldest and most striking skyscrapers. The exterior and interior are worth seeing; it’s a chance to appreciate the craftsmanship of early 20th-century architecture. Reviewers mention how they loved exploring inside, noting that “learning about the history of each was fascinating.” It’s easy to see why this stop is repeatedly praised, especially if you enjoy architecture and historical buildings.

Calders Flamingo and Modern Art

Moving into the modern era, you’ll see Alexander Calder’s Flamingo alongside Mies van der Rohe’s architectural influences. As one reviewer put it, “Modern Art meets Modern Architecture,” which sums up this part nicely. Expect a short, 10-minute stop here, but one that leaves a lasting impression—both visually and intellectually.

The Picasso Sculpture: A Monumental Highlight

One of the standout features of the tour is Picasso’s massive “Untitled” sculpture, standing 50 feet tall. It’s an instant photo-op and a piece that sparks curiosity. The sculpture’s design reflects Picasso’s influence on Chicago’s public art. Reviewers mention how seeing the sculpture in person is worth it and adds a wow factor to the walk.

James R. Thompson Center and the City’s Quirkiest Building

Another intriguing stop is the Thompson Center. It’s described as “one of Chicago’s most bizarre buildings,” and the inside is just as fascinating as the outside. The guide will tell stories about the building’s transformation—something that’s appreciated by those interested in urban development and architecture. Expect about 15 minutes here.

Chicago Theatre: A Cultural Icon

While the tour doesn’t include inside admission, the Chicago Theatre’s impressive façade makes it worth a long look. The stories about its entertainment history are often highlighted, and many reviews hint that this is a favorite photo spot. It’s a must-see for anyone interested in Chicago’s entertainment scene.

Macy’s on State Street and the Marshall Field’s Legacy

Here you’ll learn about the revolutionary department store that once claimed to be the biggest in the world. The inside scoop on Chicago’s retail history is a highlight, and the stories make the shopping experience more meaningful. The stop lasts around 10 minutes and is a favorite for those interested in commercial history.

Chicago Cultural Center: The “People’s Palace”

Concluding at the Cultural Center, this beautiful building is a visual treat. It’s often called a “library with a legacy,” and the inside is stunning, with ornate details and a sense of history. The tour wraps here, providing a perfect moment to reflect on what you’ve seen and learned.

What Makes This Tour Special?

The guide’s storytelling is consistently praised, with reviewers describing Colin as knowledgeable, personable, and humorous. Stories that range from the tragic to the humorous keep the pace lively and engaging. Many mention how Colin’s personal insights and visual adds make the experience feel like a friendly exploration rather than just a lecture.

The combination of art, architecture, and stories means that you’re not just walking past buildings—you’re understanding their significance, their history, and their artistic value. Plus, the chance to peek inside buildings usually off-limits to the public makes this tour feel exclusive.

Pricing at $33 is very reasonable, especially considering the inside visits and the amount of storytelling you get. Reviewers agree that it’s a good value, especially since many stops include gorgeous interiors that normally require separate tickets.

The small group size ensures personalized attention and makes for an intimate experience. This is perfect if you prefer not to be part of a large crowd, especially when exploring detailed stories or taking photos.

Practical Details and Considerations

Duration and Distance: The tour runs for about two hours, covering roughly 2 miles. It’s a relaxed pace, but be prepared for some standing and walking, including stairs and elevators in certain buildings. Reviewers note that the walk is “easy” and breaks are well timed, so it’s accessible for most travelers with moderate physical fitness.

Weather: Since the tour involves outdoor stops, good weather is important. If it’s rainy or extremely cold, the guide will offer alternative indoor visits or reschedule. Keep in mind that the experience is partly outdoor, so dress accordingly.

Booking in Advance: The tour is often booked about 3 weeks ahead, so plan early if you want to secure a spot, especially during peak seasons.

Booking and Cancellation: You can cancel up to 24 hours in advance for a full refund, which is flexible if your plans change. Just be aware that cancellations less than 24 hours before are non-refundable.

Who Will Love This Tour?

This experience is best suited for art lovers, architecture enthusiasts, and curious travelers who enjoy storytelling and inside access. It’s ideal if you want a leisurely, personalized walk that combines visuals with engaging narratives. Families with older children who can handle a moderate pace may find it enjoyable, but it’s mostly geared toward adults or older teens.

If you’re looking for a quick, superficial overview of Chicago, this isn’t it. Instead, you get in-depth stories and behind-the-scenes insights that bring the city’s landmarks to life.

FAQs

Is this tour suitable for children?
The tour involves walking and some indoor exploration, so it’s best for older children or teenagers comfortable with moderate physical activity. It isn’t explicitly marketed as family-friendly, but curious teens who love art and stories should enjoy it.

How long is the tour?
The tour lasts approximately 2 hours and covers about 2 miles.

Can I choose the time of the tour?
Yes, there are morning and afternoon options, making it flexible to fit into your day.

Is it accessible for people with mobility issues?
The tour involves stairs and elevators, and the physical activity is moderate. Travelers should have a moderate physical fitness level.

What’s included in the price?
The tour price covers the guided walk, access to indoor spaces (like the Marquette Building and Cultural Center), and the storytelling. No additional tickets are required for the buildings included.

What if it rains?
The tour requires good weather. If canceled due to poor weather, you’ll be offered an alternative date or a full refund.

How far in advance should I book?
Most bookings are made about 21 days in advance, so it’s wise to plan ahead, especially during busy seasons.

Final Thoughts

If you’re after an experience that combines art, architecture, storytelling, and a good dose of humor, Colin’s downtown Chicago tour is an excellent choice. The personal touch and inside access make it more than just a stroll—it’s a curated journey through the city’s visual and historical treasures.

The extensive praise from past travelers speaks volumes: knowledgeable guides, great value, and a fun atmosphere are what make this tour worth considering. It’s especially good for those who appreciate stories behind the buildings, love to learn, and want to see a side of Chicago most travelers miss.

However, remember it’s a moderate activity with outdoor elements, so dress appropriately and be prepared for the weather. If those conditions suit you, this tour offers a great way to spend a couple of hours exploring Chicago’s vibrant core in a relaxed, friendly setting.

In essence, this is a tour for the curious, the art lover, and anyone wanting a more intimate look at Chicago’s architectural and cultural gems. Whether you’re new to the city or a local wanting to rediscover it, Colin’s storytelling approach makes for a memorable experience.