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Century of Contrasts South Loop Walking Tour

A walk back in time through Chicago's South Loop.

From the Great Chicago Fire to the disco inferno, this curated South Loop walking tour takes you to experience incredible architecture and forgotten stories. As we look at the past, we’ll see how people, projects and ideas within the city of “Make No Little Plans” have both succeeded big and failed miserably over its history. Sights include the famous and lesser-known Chess Records locations, ornate terra cotta facades of Motor Row, and the opulent interiors of the Glessner House on Prairie Avenue. This new tour is quickly becoming one of our most popular!


This area of Chicago is like an open air museum of architecture and relics of various periods of Chicago history. You’ll see architecture from 1870s mansions to early 1900s factories to 1970s public housing. On our tour, we’ll consider how the ups and downs of neighborhood change are the same as anything in life. You have to take risks. Most symbolically, Chicago failed with the Great Chicago Fire. But we’ll talk about a company that rose from the ashes to become one of the largest in its industry still today.

We’ll visit the sites of failure and success, from the course of Muddy Waters career with Chess Records as a blues musician, to the course of cars in shaping cities for better and for worse. Guests will learn of the dramatic fall of the mansion district, as beautiful greystones went from high-class soirees to flophouses and publishing offices.

The neighborhood’s Prairie Avenue once boasted “Millionaire Row.” At the peak of the Gilded Age in the late 19th century, some of the wealthiest people in American history built palatial mansions here. The contrast of a century later brings us on our tour to the oft-overlooked 1970s – a crucial and overlooked time in Chicago history. It was a time of transition. The neighborhood was spattered with industrial buildings, shuttered train stations, parking lots, and McCormick Place, the just-opened, colossal convention center. Despite this unbecoming state in the 1970s, the forces unleashed at that nadir of urban decay led to the vibrant and redeveloped neighborhood we experience on our walking tour.

This quick, 1.75-hour curated experience starts in the lobby of the Marriott Marquis, 2121 S Prairie Ave, and ends at the Clarke House, 1827 S Indiana.


Our walking tour is a like a mobile documentary. We show media on iPads. We design the content using archival resources in order to share untold stories. This tour is a curated narrative of neighborhood change. Tour guides go beyond the dates and names of wealthy families on Prairie Avenue. 

Our professional tour guides truly love and know Chicago architecture and history. They are not volunteer docents. We are all educators and committed to sharing secret stories behind buildings and new ideas for architectural appreciation.

As you look into possibilities for your Chicago private group event, this quick guide may help you determine if we would be the best tour company for your event. Dates book up quick, so call us now to reserve a spot for your group tour!

In business since 2010, we are a top-rated Chicago tour company. We hold five-stars on both TripAdvisor and Google. 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.


1.75 hours


.9 miles


  • Step into the Glessner House, an 1870s mansion
  • Ornate early auto dealerships on Motor Row
  • Both former locations of Chess Records, a blues mecca
  • The Clarke House, the oldest built in Chicago
  • Unexpected architectural relics

Stories & Ideas

  • High society gossip of the Gilded Age
  • Kitschy 1970s nostalgia and funky products
  • Changes in residential architecture and decor
  • Understand design concepts behind Prairie Avenue
  • The roots of the historic preservation movement

Tour Includes

  • 15-minute tour inside the Glessner House
  • Engaging tour guide commentary
  • Shared use of iPads with photos
  • Special gifts

Tour Location

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Call: 312.350.1131
E-Mail: [email protected]