Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour - The Chicago Theatre and Its Entertainment Roots

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

Explore Chicago’s architecture, art, and history on this 2-hour walking tour with Colin, covering iconic landmarks and hidden stories for $33 per person.

The Walkin’ with Colin: Chicago History-Mystery-Comedy-Tragedy Tour offers an engaging and informative exploration of downtown Chicago for just $33 per person. This 2-hour walking experience combines art, architecture, and storytelling, taking you through famous landmarks and lesser-known secrets. With a small group size of up to 10 travelers, you’ll enjoy personalized insights from a guide who is both knowledgeable and personable. The tour’s average booking time of 21 days in advance indicates strong interest and a well-organized experience. Whether you prefer morning or afternoon, this tour’s flexible schedule makes it suitable for a variety of plans.

What sets this tour apart is the diverse stop list, from iconic sculptures to historic buildings, paired with storytelling that weaves humor, tragedy, and mystery. Visitors appreciate the interior visits of notable buildings, which add depth far beyond typical exterior sightseeing. Keep in mind that the tour involves moderate physical activity, covering about 2 miles with some stairs and outdoor walking, so it’s best suited for those with average mobility.

Key Points

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour - Key Points

  • Affordable price at $33, with options for morning or afternoon departures
  • Approximately 2 hours in length, covering key downtown Chicago highlights
  • Small group size ensures personal attention and engaging storytelling
  • Visits to interior spaces of buildings like the Marquette Building and Cultural Center
  • Tour includes notable artworks such as Calder’s Flamingo and Picasso’s sculpture
  • Highly praised guide known for knowledge, humor, and storytelling flair

Exploring Chicago’s Art Pieces: Calder, Picasso, and Chagall

This tour shines in its focus on art installations and mosaic murals. The first stop features Marc Chagall’s Four Seasons mosaic mural, a stunning piece of public art that immediately captures visitors’ attention. Next, travelers see Alexander Calder’s Flamingo and Mies van der Rohe’s architecture, perfectly blending modern art with modern design. The grand Picasso sculpture, called “Untitled,” measures 50 feet tall and offers a powerful visual statement. These artworks are not just sights; they are stories told through public sculptures and murals, revealing Chicago’s vibrant artistic side.

The tour emphasizes the integration of art and architecture, giving visitors a visual feast that enhances the city’s atmosphere. The combination of interior and exterior views makes for a well-rounded experience, especially for those interested in public art and design.

Inside the Marquette Building and Other Historic Sites

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour - Inside the Marquette Building and Other Historic Sites

The Marquette Building is presented as one of Chicago’s most magnificent skyscrapers, with an emphasis on both its exterior façade and interior design. During the visit, the guide highlights its architectural significance and historical importance. The interior features beautiful design details that are often missed by casual passersby, making this stop a highlight for architecture buffs.

Another intriguing stop is the James R. Thompson Center, where visitors learn about its bizarre architecture and the remarkable transformation of its foundation. These visits provide a deeper understanding of Chicago’s building history and urban development.

The Chicago Theatre and Its Entertainment Roots

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour - The Chicago Theatre and Its Entertainment Roots

The Chicago Theatre stands out as an iconic entertainment venue. The tour offers a detailed look at its impressive façade and shares stories about Chicago’s great entertainers who performed there through the years. Although admission isn’t included, the guide’s narration makes this stop come alive, connecting the architecture to the city’s cultural history.

Discovering the Marshall Field’s Department Store

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour - Discovering the Marshall Field’s Department Store

The stop at Macy’s on State Street delves into the legacy of Marshall Field’s, the revolutionary department store that once claimed to be the largest in the world. This building’s history reflects Chicago’s fashion and retail evolution, and the guide explains how it helped shape the modern department store model. This stop offers a fascinating retail history lesson in a beautiful historic setting.

Chicago Cultural Center: A Historic Library

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour - Chicago Cultural Center: A Historic Library

The final stop at the Chicago Cultural Center invites visitors inside a beautiful building with a significant legacy. Known as a cultural hub, this site showcases glorious architecture, including its famous stained glass domes. The center holds historical significance and provides a peaceful, inspiring space to conclude the tour.

Practical Information: Meeting Point, Group Size, and Accessibility

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour - Practical Information: Meeting Point, Group Size, and Accessibility

The tour begins at 1 N Dearborn St and concludes at the Chicago Cultural Center at 78 E Washington St. The group size is capped at 10 travelers, fostering an intimate experience. It is accessible via public transportation, making it convenient for visitors staying in or near downtown Chicago. The tour involves moderate physical activity, with walking over about 2 miles and some stairs or elevators at certain stops.

Travelers should have moderate physical fitness to comfortably navigate both outdoor and indoor areas. Since the tour operates rain or shine, it’s advisable to check the weather forecast before booking.

Why This Tour Stands Out in Chicago

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour - Why This Tour Stands Out in Chicago

What makes Walkin’ with Colin a standout choice is the expert storytelling combined with interactive visits to notable buildings and artworks. The guide, Colin, is praised for his knowledge, humor, and personable style, making the experience both informative and entertaining. Many reviews highlight that Colin’s storytelling reveals hidden stories and symbols that many locals and travelers alike might overlook.

The cost-to-value ratio is high, given the comprehensive nature of the stops and the interior access to impressive sites. Visitors also benefit from flexible scheduling with morning and afternoon options.

Final Thoughts on the Walkin’ with Colin Tour

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour - Final Thoughts on the Walkin with Colin Tour

This tour offers an affordable, engaging, and well-organized way to experience downtown Chicago’s architecture, art, and history. The small group setting ensures plenty of personalized attention and opportunity for questions. It’s especially suited for those interested in architecture, public art, and Chicago’s cultural landmarks.

While it’s a walk of about 2 miles, the pace is easy and broken up with interior visits and storytelling, making it accessible for most participants. Visitors leave with a deeper appreciation of the city’s creative and historical spirit, along with beautiful photos captured during the stops.

Overall, Walkin’ with Colin delivers a fun, informative, and visually stunning exploration of Chicago’s core sights. It is particularly recommended for locals wanting a fresh perspective and first-time visitors eager to uncover Chicago’s stories.

Ready to Book?

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



5.0

(125)

98% 5-star

“The second hour was better than the first, although the first was great. Collin saved the best for last, so dont think about skipping out.”

— Ann E, May 2025

Frequently Asked Questions

How long does the tour last?
The tour lasts approximately 2 hours.

What is the price of this tour?
The ticket costs $33 per person.

Where does the tour start and end?
It begins at 1 N Dearborn St and ends at the Chicago Cultural Center, 78 E Washington St.

Are interior visits included?
Yes, stops at Marquette Building, Cultural Center, and other landmarks include interior visits.

Can I choose the time for the tour?
Yes, there are morning and afternoon options available.

What is the group size?
The maximum group size is 10 travelers.

Is this tour suitable for all physical fitness levels?
It requires moderate physical activity, involving walking and stairs, so it’s best for those with average mobility.

Do I need to cancel in advance?
Yes, free cancellation is possible up to 24 hours before the start time.
If canceled less than 24 hours prior, the refund is not available.

What makes this tour special?
The blend of art, architecture, and storytelling, along with interior access and Colin’s engaging style, make this a unique way to experience downtown Chicago.

Is the guide knowledgeable?
Yes, reviews consistently praise Colin for his expertise, humor, and storytelling ability.