Prairie District Chicago Neighborhood Tour

Motors, Music and Mansions

Prairie District: Street of the Elite

Tour runs Saturday.  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 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

  • Masks required on train, even if vaccinated
  • Masks may be required in some public spaces
  • Hand sanitizer available
  • Health & Safety Page

Small Bites

  • Chicago deep dish pizza
  • Choice of beverage
  • Sweet treat

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, 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 - single bookings subject to cancellation if minimum is not met
  • Maximum tour size - 6 guests
  • Children must be 12 years or older and accompanied by an adult (age 18 or older)

Tour Meeting Point and Stops