Why choose this Chicago tour ?

This extraordinary tour of the Prairie Ave District is one not to be missed.

Get a sense for how Chicago’s wealthiest residents lived around the turn of the century and what remains today. This unique Chicago tour begins with an exploration of one of the city’s newly-revitalized spaces: The stunning Chicago Athletic Association Hotel.

A short ride on the Green Line takes us to the Prairie Ave District, home to many historic sites such as Motor Row, the former Chess Records and the oldest house in the city. As we wander along Prairie Ave, we’re treated to historic mansions and a beautiful park. The highlights of the tour, however, are TWO private, docent-led mini tours at the national landmark Second Presbyterian Church (with its many Tiffany windows) and the Glessner House. We’ll also take a mid-tour break at a local employee-owned/woman-owned cafe. Then we board the train back to the Loop for our final stop (and a sweet treat) at the elegant Palmer House Hotel.



Make the most of your Chicago adventure

What makes Chicago Prairie Ave District Walking Tour: Street of the Elite a unique experience ?

Meet your guide and kick things off with a tour of this historic hotel. Then we’ll head to Washington & Wabash to board the Green line train to the Prairie District.

After a brief stroll from the Cermak L station, guests will learn about the building that produced some of the most well-known and influential Blues music of Chicago.

Guests will receive a private docent-led mini tour.

Take a break and enjoy a snack at this unique employee-owned/woman-owned cafe (purchases optional).

Guests will receive a private docent-led mini tour.

Guests will see the oldest house in Chicago and learn how elite Chicagoans lived at the turn of the century.

After our train ride back to the Loop, we’ll explore the beautiful interior of this famous building and end the tour with a sweet treat.

Tour Description & Additional Info:

  • Public transportation options are available nearby
  • Not recommended for travelers with spinal injuries
  • Not recommended for travelers with poor cardiovascular health
  • Travelers should have at least a moderate level of physical fitness
  • Should be able to climb stairs as not all train stations are equipped with elevators


Options To Choose for Your Trip:

  • Chicago Prairie Ave District Walking Tour: Street of the Elite
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Chicago Prairie Ave District Walking Tour: Street of the Elite Inclusions:

Included with Your Ticket

  • Transit tickets
  • Church and Glessner House donation/fee
  • Local expert guide
  • Food and beverages

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Special Instructions:

    Please arrive at the tour meeting point 15 minutes early to sign a liability waiver if you have not already done so online.

    Please be advised..

  • This Tour is Provided by L Stop Tours.
  • Tour Timezone & Starts at America/Chicago.
  • Mobile or paper ticket accepted.
  • For a full refund, cancel at least 24 hours before the scheduled departure time.
  • This Tour is Rated 5 Stars based on 19 valid reviews on VIATOR.
  • Minimum 1 Travelers is required to book.
  • Maximum 10 Travelers is accepted for booking.