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Free Chicago Walking Tour Inside a Historic Skyscraper

View the painstaking restoration of a 19th-century masterpiece

This free Chicago walking tour of the Monadnock Building showcases its monumental architecture, gorgeous interiors and fascinating history. The groundbreaking restoration of this 19th-century skyscraper demonstrates the value of preserving historic architecture. Gratuities for this brief and mostly indoor tour, which is available for a limited time, will benefit Preservation Chicago!  


On this free Chicago walking tour, you’ll discover the elegant architecture of the Monadnock Building, one of the oldest skyscrapers of downtown Chicago. During your 30-minute-long architectural walking tour, your professional tour guide will share the larger-than-life story and structure of this classic 1890s skyscraper. You’ll enter the building to experience the Monadnock’s inspiring interiors. The tour will be inside 75% of the time, meaning you’ll be comfortable on this tour even in inclement weather.

The tour group starts in a cafe, and then steps outside to consider the monumental architecture of the Monadnock’s exterior. Once inside the Monadnock, it’s like stepping back to 19th-century Chicago. Tour guests see architectural details like intricate brass doorknobs, glamorous aluminum stairs and old-fashioned mailboxes. You’ll also see old-time businesses like a haberdashery and florist. 

Unique to this tour, as compared to other architectural building tours, is that Chicago Detours will share the big ideas of design behind historic preservation. In the 1980s, the building’s owner undertook a painstaking restoration under the direction of  award-wining preservation architect John Vinci. Thanks to their foresight, business acumen and creativity, the Monadnock has the authentic feeling of a 19th-century commercial building while being comfortable and functional for the building’s current tenants. To design this free walking tour, Executive Director Amanda Scotese consulted with two experts on the Monadnock’s transformation: official city historian Tim Samuelson and Preservation Chicago Executive Director Ward Miller.

The Monadnock Building demonstrates how crucial it is to preserve Chicago’s incredible architecture. Chicago Detours is committed to supporting efforts to save our city’s historic architecture. Thus our tour guides are donating 100% of all gratuities received on this free walking tour to Preservation Chicago. This non-profit organization “protects and revitalizes Chicago’s irreplaceable architecture, neighborhoods and urban spaces.”

Please note that because we are walking and standing on the tour we have to call this a “walking tour” but we are not walking much distance at all.

This tour is free and offered weekly on Fridays from November 2nd until December 8th. Reservations are required! Please book now.


As a top-rated tour company, with professional (not volunteer) tour guides, why are we offering this Chicago walking tour by foot for free?

  • To give back to the community! Tour guides will donate all gratuities to Preservation Chicago.
  • To welcome new walking tour guests! Come experience our style of walking tour.
  • To thank our previous tour guests and see them again!
  • Lastly, the Monadnock Building is our office home. We love sharing our appreciation for the Monadnock Building’s incredible architecture on this free walking tour. 


Our expert tour guides are highly trained, smart, fun and passionate about Chicago architecture and history. Be careful of volunteer tour docents and guides with free Chicago walking tour companies – while some are excellent, they do not have a quality guarantee.

In business since 2010, we are proud to be a top-rated Chicago tour company with five-stars on Yelp and TripAdvisor. Many of our Chicago architecture walking tours integrate historic bars, food, and music history. We hope you’ll join us to explore stories and places locals don’t even know, both downtown and in Chicago neighborhoods!

If you’re looking for something more in-depth, check out our regularly scheduled (and not free) public tours of Chicago architecture and neighborhoods, available day and evening throughout the week. We can offer this as a private tour, too!


.5 Hour


.2 mile



  • Days & Times

  • Fridays in November


  • Architecture by Chicago masters
  • Ornate historic architectural details
  • Dramatic cast-aluminum staircases
  • Original 19th-century mosaic tile floor
  • Old-timey businesses like a haberdashery

Stories & Ideas

  • The preservation of historic architecture
  • Chicago’s rapid growth at the end of the century
  • Connections between early Chicago architecture and Modernism
  • Challenges of precise engineering in the 19th century

Tour Includes

  • Engaging tour guide commentary
  • Discount for our other walking tours

Tour Location

Walking tour begins inside Dollop Coffee in the Fisher Building, 343 S Dearborn (use the entrance on Van Buren) - NOTE that the tour begins across the street from the Monadnock.
We will end inside the Monadnock, 53 W Jackson.

Book Now


Call: 312.350.1131
E-Mail: [email protected]