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New in ’20! Century of Contrasts South Loop Walking Tour

From corporate contemporary to Gilded Age glamour in a few short blocks

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 area of Chicago is like an open air museum of architecture and relics of various periods of Chicago history, 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 a company 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 wit 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 in this bucolic area. 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.

The Century of Contrasts South Loop Walking Tour can now be booked for private groups. Contact us at 312.350.1131 for more details on booking this South Loop walking tour as a private event.


1.75 hrs


.9 mile



  • Days & Times

  • 1st and 3rd Sundays, May- November 1st 2020


  • Step into the Glessner House, an 1870s mansions
  • Ornate early auto dealerships on Motor Row
  • Both the famous and less-known places 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

Stories & Ideas

  • High society gossip of the Gilded Age
  • Kitschy 1970s nostalgia and funky products
  • The evolution of city life over a century
  • 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 video and photos
  • Special gifts

Tour Location

This walking tour meets inside the Food Hall of Marriott Marquis, 2121 S Prairie Ave.
We end on the steps of the Clarke House, 1827 S Indiana.

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Call: 312.350.1131
E-Mail: [email protected]