Walkin’ with Colin: Chicago Tour du Jour

If you’re after an authentic, in-depth stroll through downtown Chicago, Walkin’ with Colin’s Tour du Jour offers a compelling mix of history, art, architecture, and local lore—all packed into a lively 2-hour walk. It’s a tour that’s consistently praised by travelers, earning a perfect 5-star rating, and for good reason. What sets this experience apart is not only the knowledgeable guiding but also the way it weaves together stories that breathe life into the city’s buildings and public spaces.

What we really love about this tour is how Colin, the guide, combines entertainment with education—all delivered with genuine enthusiasm. You’ll find yourself genuinely engaged, as stories of daring feats and curious calamities unfold around you. One slight consideration is that the tour is tailored for those who are able to walk comfortably and can tolerate a couple of hours on their feet. But if you’re looking for a friendly, small-group experience that’s perfect for history buffs, art lovers, or anyone curious about Chicago’s character, this tour hits the mark.

This experience is especially suited for travelers who want more than just a surface-level sightseeing—it’s ideal for those who enjoy storytelling, exploring iconic landmarks, and discovering lesser-known tidbits along the way. Families with older children (over 13) and anyone with an interest in architecture and local culture will find plenty to love.

Key Points

• Authentic storytelling from a passionate local guide makes the history and architecture come alive.
• Stunning public art and architecture including works by Picasso, Chagall, Calder, and DeBuffet.
• A well-paced 2-hour walk through Chicago’s vibrant downtown, with opportunities to explore both famous and hidden sites.
• Impressive views both inside and outside notable buildings and public spaces.
• Inclusive experience with all building entries covered, plus flexibility with reservations thanks to a full refund policy.
• Small group size (limited to 10), ensuring personalized attention and interaction.

A Deep Dive into the Experience

Starting Point: 1 N Dearborn St

This is a convenient meeting spot, right beside the bus stop and Blue Line station, making it easy to access from anywhere in the city. Colin, the guide, is easy to spot—look for his Red, White, and Blue Backpack under the iconic red “1” roof. From here, the journey begins, setting the tone for a lively, engaging exploration.

Exploring Chicago’s Masterpieces: Chagall’s Four Seasons

The tour kicks off with Marc Chagall’s Four Seasons, a colorful, captivating piece of public art. Colin’s narrative here pulls in the cultural significance of murals and how they shape city identity. This stop is about 15 minutes, giving enough time to admire the art and hear stories about its creation and impact on Chicago’s cultural landscape.

Marquette Building: A Landmark of Architectural Elegance

Next, we wander to the Marquette Building, a prime example of early 20th-century architecture. Despite its rich design, it’s often overlooked by the typical tourist. Colin offers insights into its design elements and historical importance, making it clear why preservation matters. The stop lasts around 10 minutes, but you’ll leave with a sense of the building’s significance in Chicago’s architectural history.

Calder’s Flamingo: A Sculptural Highlight

The tour then moves on to Alexander Calder’s Flamingo, an instantly recognizable sculpture that introduces an element of modern art into the mix. Colin explains Calder’s unique style and how this piece contributes to Chicago’s public art scene. This brief stop of about 10 minutes allows for close-up viewing and a bit of humor from the guide about Calder’s whimsical approach.

Chicago Picasso Statue: An Iconic Piece

A visit to Chicago’s Picasso statue offers a chance to reflect on abstract art’s role in urban spaces. Colin shares stories about the statue’s controversial debut and its evolution into a beloved city symbol. It’s a popular photo spot, and the guide’s commentary makes the experience richer.

Architectural and Cultural Highlights: Chicago Temple Building & The Chicago Theatre

As you stroll past the Chicago Temple Building and The Chicago Theatre, Colin’s knowledge shines. The former is notable for its religious history and architectural grandeur, while the latter’s marquee and interior are cinematic legends. These stops are about 10 minutes each, giving time for photos and absorbing stories about Chicago’s entertainment and spiritual architecture.

Macy’s and the Chicago Cultural Center

The tour continues through the bustling Macy’s flagship, a historic department store with a storied past, and culminates at the Chicago Cultural Center. The cultural center is a treasure trove of art, architecture, and local events, making it a fitting end point. Colin’s narration covers everything from art installations to city history, ensuring your walk finishes on a high note with plenty of options for further exploration.

Value for Money

At $33 per person, this tour offers remarkable value. All building entries are included, so there are no hidden fees, and you get a genuinely immersive experience led by a top-rated guide. The tour’s length and content make this a practical option for travelers who want a meaningful introduction to downtown Chicago without long, exhausting excursions. Plus, with a 24-hour full refund policy, it’s flexible enough to book with confidence.

What Makes It Stand Out?

The combination of entertaining storytelling and expert guidance sets this tour apart. Colin’s enthusiasm is contagious, and travelers consistently mention how much they appreciated his knowledge and friendly demeanor. The small group size (capped at 10) ensures everyone can ask questions and get personalized insights.

Practical Considerations

While the tour is suitable for most people with a reasonable level of fitness, it involves walking on city streets and around various architectural sites. Children under 13 might not find it as engaging, and those with colds or mobility issues should consider alternative options. The tour runs at different times—checking availability beforehand helps plan your day.

Who Should Consider This Tour?

If you love architecture, history, or public art, this tour is an excellent choice. It’s perfect for travelers who want a deeper understanding of Chicago’s soul beyond the usual landmarks. Photography enthusiasts will enjoy the countless photo-worthy spots, and culture vultures will appreciate the stories behind each piece.

It’s especially suited for those who value small-group experiences and personal interaction with guides. Whether you’re visiting Chicago for the first time or returning for a deeper dive, Walkin’ with Colin offers a friendly, insightful way to explore the city’s downtown core.

The Sum Up

Walkin’ with Colin’s Tour du Jour is a lively, well-curated experience that offers more than just sightseeing. It’s an engaging blend of stories, art, and architecture, all delivered by a passionate guide. The tour’s emphasis on insider stories and stunning visuals make it a standout option for anyone seeking a meaningful Chicago experience in just two hours.

Priced reasonably and with a flexible booking policy, it’s an accessible way to get to know some of Chicago’s most iconic and overlooked sites. The small group format ensures personalized attention, making it perfect for curious travelers who want a deeper connection to the city.

Whether you’re a first-timer or a seasoned visitor, this walk provides genuine insight, beautiful sights, and a taste of Chicago’s unique character—definitely worth considering for your trip.

FAQ

Is this tour suitable for children?
It’s recommended for travelers over 13 years old. Younger children might find the pace or content less engaging.

How long does the tour last?
The tour runs for approximately 2 hours, making it a manageable and relaxed experience.

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

Is the tour wheelchair accessible?
Yes, the tour is accessible for wheelchairs.

What is included in the price?
All building entries are included, along with the services of a top-rated, professional guide.

Can I cancel if my plans change?
Yes, cancellations are accepted up to 24 hours in advance for a full refund.

How many people will be in the group?
The tour is limited to 10 participants, ensuring a more intimate experience.