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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 contrasts the social history and architecture of two crucial periods in Chicago history. Private group tour guests will experience incredible architecture among the famed historic districts of Motor Row and Prairie Avenue. Beyond the architecture, guests will discover the unexpected stories of the people who lived and worked in Chicago’s South Loop from 1871 to 1971.

Available starting in August 2019.


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 in this bucolic area. 

By the 1970s, 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 choices made and forces unleashed at that nadir of urban decay led to the vibrant and redeveloped neighborhood of today.

1971 was a crucial and overlooked year in Chicago history, a time of transition. City leaders opened America’s biggest convention center, a Modernist corporate acropolis. The roots of the historic preservation movement were taking form mere blocks away. The closure of passenger railroad lines marked the end of an era that defined Chicago’s role in the country, and began the era that we now live in. 

Private groups will learn massive histories and inside stories at mom and pop factories and visit both the famous and less-known locations of Chess Records. Guests will learn of the dramatic fall of the mansion district, as beautiful greystones went from high-class soirees to flophouses and publishing offices. This private group tours presents new perspectives on how the South Loop became the vibrant neighborhood it is today. 


This South Loop Walking Tour can also visit a historic bar as an upgrade for adult beverages and appetizers. Inquire for details on the historic bar tour upgrade for your group!


Our walking tour is a like a mobile documentary, with various media, archival resources, and untold stories. We will share a curated narrative of neighborhood change. Tour guides go beyond the dates and names of wealthy families on Prairie Avenue. 

Our highly-trained, expert tour guides are smart, fun and passionate about 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 Chicago tour company for your group. Dates book up quick, so call us now to reserve a spot for your group event!

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.


1.5 hours


.9 miles


  • Prairie Avenue mansions of the 1880s
  • Ornate early auto dealerships on Motor Row
  • Both the famous and less-known locations of Chess Records, home of Chicago blues
  • The Clarke House, the oldest built in Chicago
  • Landscaped gardens of the Chicago Women’s Park
  • Unexpected architectural relics
  • High society gossip of the Gilded Age
  • Kitschy 1970s nostalgia
  • The turning point in public housing policies
  • Funky inventions from Chicago
  • The roots of the historic preservation movement

Tour Includes

  • Engaging tour guide commentary
  • Shared use of iPads with video and photos
  • Special gifts

Tour Location

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Call Us: 312.350.1131
E-Mail Us: [email protected]