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Aug 24 & Sept 21 – South Loop Walking Tour

From the Great Chicago Fire to the disco inferno, this curated South Loop walking tour explores the social history and architecture of a century of Chicago history, from the Gilded Age glamour of the 1870s and the postindustrial grit of the 1970s. On this tour, you will experience incredible architecture in the famed South Loop historic districts of Motor Row and Prairie Avenue. You will also step back in time within the rooms of a Gilded Age mansion. Normally available only for private groups, this unique South Loop walking tour will be available to the public for one day only. Space is limited, so sign up now!

The Saturday, August 24 tour has SOLD OUT. We have added a second date on Saturday, September 21, at 12:45pm.

South Loop tour guests will discover the unexpected stories of the people who lived and worked in the area from 1871 to 1971. 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.

The early 1970s was a crucial and overlooked time in Chicago history. It was a time of transition. City leaders opened McCormick Place, America’s biggest convention center. 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.

Learn the 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 walking tour presents new perspectives on how the South Loop became the vibrant neighborhood it is today.

Tour begins inside the Marriott Marquis, 2121 S Prairie Ave, and ends at the Clarke House, 1827 S Indiana.

This is an exclusive tour available only on August 24 as a special event. Space is limited and reservations are required. The Century of Contrasts South Loop Walking Tour can 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

  • Sat. Aug. 24

    Sat. Sept. 21

    Sat. Aug. 24

    Sat. Sept. 21


  • 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
  • Changes in residential architecture and decor
  • Funky inventions from Chicago
  • 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.

Book Now

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