Prairie District Chicago Neighborhood Tour

Motors, Music and Mansions

Prairie District: Street of the Elite

Click here to learn more about touring safely and also our Prairie District Walking-Only Tour option.


To minimize health concerns due to COVID-19, all of our tours will be limited to 6 or fewer people. Your tour will be private and exclusive to your group.

Along with offering our standard tours, we will also be providing walking tours at a discounted rate for you and your group. You can learn more about our new health and safety standards by visiting our COVID Reopening page.

With our Chicago Prairie District tour, you’ll get a sense of how the city’s wealthiest residents lived around the turn of the century and what remains today. This unique Chicago city tour begins with an exploration and coffee at one of the city’s newly-revitalized spaces: The beautiful Chicago Athletic Association Hotel.

Like all of our other Chicago walking tours, we take a short L ride to the Chicago Prairie District, which is home to many historic sites such as Motor Row, the former Chess Records, the oldest house in the city, the landmark Second Presbyterian Church and the Glessner House. After enjoying some traditional Chicago deep dish pizza, we’ll board the train back to the Loop. There, we’ll peek inside a historic hotel and grab a sweet treat (with a sweet story) to wrap up the Chicago city tour.

Want to learn more about the Chicago Prairie District before you embark on our Chicago walking tour? Visit our Chicago neighborhood guide to learn more!


Tour Highlights

Explore Two Neighborhoods

  • South Loop
  • Prairie District

Two Docent-Led Mini Tours Included

  • Second Presbyterian Church
  • Glessner House

Tour Options

Small Bites

  • Coffee
  • Chicago deep dish pizza
  • Sweet treat

Book Prairie District: Street of the Elite

Duration: 4 hours

Extra time built in for train travel

Price: Adult $90 | Youth $90

  • Days of operation: Wed, Sat
  • Save 15% on Wednesday tours
  • Start time: 10:30am
  • Tours begin and end in the Loop (See below)
  • Walking distance: 1.6 miles
  • Tour price includes food, beverages and transit fees
Prairie District: Street of the Elite Logo

Additional Information

Ticket Purchase Requirements

  • Must be able to climb stairs
  • Tour requires minimum of 2 guests to run - single bookings subject to cancellation if minimum is not met
  • Youth (age 12 and over) must be accompanied by an adult (age 18 and over)
  • Please bring a valid form of ID

Tour Meeting Point and Stops