Prairie District Chicago Neighborhood Tour

Motors, Music and Mansions

Prairie District: Street of the Elite

Tour runs Saturdays.  Book now!

Click here to learn more about touring safely.


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 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 Chicago walking tours, we begin with a short L ride to our destination neighborhood. The Chicago Prairie District 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 wrap up this Chicago Walking tour at the famous Palmer House Hotel.

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


Tour Highlights

Explore Two Neighborhoods

  • South Loop
  • Prairie District

Two Docent-Led Mini Tours Included

  • Second Presbyterian Church
  • Glessner House

Health & Safety

Small Bites

  • Chicago deep dish pizza
  • Choice of beverage
  • Sweet treat (option to purchase)

Book Prairie District: Street of the Elite

Duration: 4 hours

Extra time built in for train travel

Price: Adult $90

  • Tour price includes transit fees, church donation & museum entrance fees, food & beverages
  • Days of operation: Sat
  • Start time: 10:30am
  • Tours begin and end in the Loop
  • Walking distance: 1.6 miles
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
  • City of Chicago requires masks on all mass transit
  • Children must be 12 years or older and accompanied by an adult (age 18 or older)

Tour Meeting Point and Stops