Prairie Avenue District Walking Tour: Chicago’s Gilded Age Elite

Recommended by 100% of travelers

Chicago, USA

4 hours (approx.)
Mobile ticket
Offered in: English

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Overview

Step off the typical tourist trail, and discover one of Chicago’s oldest and most scenic neighborhoods, on this walking tour of the Prairie District. Meet your guide in the morning at the Chicago Athletic Association, and set off with just a small group for company. The Prairie District is just a short L ride away; you can look forward to seeing the Second Presbyterian Church, Glessner House, Motor Row, and otherwise discovering how Chicagoans lived at the turn of the 20th century.

Discover the highlights of Chicago’s evocative Prairie District
This small-group tour will have a maximum of just 8 participants
Learn all about the district’s turn-of-the-century history and architecture
Grab a snack and a drink at a unique, neighborhood cafe

What's Included

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

Gratuities
Food and beverages

Meeting and Pickup

Meeting point

Chicago Athletic Association - The Unbound Collection by Hyatt
12 S Michigan Ave, Chicago, IL 60603, USA
Find your guide inside lobby, immediately to left

End point

Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL 60603, USA
We end our tour with a sweet treat at this beautiful historic building

Operating hours
.10:00 am

Itinerary

Chicago Athletic Association - The Unbound Collection by Hyatt

50 minutes • Admission Ticket Included

Chess Records

30 minutes • Admission Ticket Free

Second Presbyterian Church of Chicago

40 minutes • Admission Ticket Included

The Spoke & Bird (South Loop)

30 minutes • Admission Ticket Free

Glessner House Museum

40 minutes • Admission Ticket Included

Clarke House Museum

10 minutes • Admission Ticket Free

Palmer House Hilton Historic Lobby

40 minutes • Admission Ticket Free

Additional Info

Confirmation will be received at time of booking
Not wheelchair accessible
Near public transportation
Not recommended for travelers with back problems

No heart problems or other serious medical conditions
Travelers should have a moderate physical fitness level
Should be able to climb stairs as not all train stations are equipped with elevators
This tour/activity will have a maximum of 10 travelers

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Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

Traveler Photos

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Reviews

5.0

based on 24 reviews

Total reviews and rating from Viator & Tripadvisor

We perform checks on reviews

Great tour of the Prairie District

Teresa_B, Oct 2025

Tour guide Tom, a native of Chicago, was very knowledgeable. He shared many stories and facts about Chicago. He was gracious and checked in to make sure we were comfortable during the walking. Highly recommend this tour.

A completely new Chicago perspective!

Marla_A, Jun 2025

This was a unique “off the tourist” experience. We loved every minute. Our guide Tom was a wealth of information, had an iPad of historic photos to share, and we took the L rail with him and then had docents scheduled as part of the tour at both the Glessner House & Presbyterian Church. Can’t wait to do another tour! We have spent many years going to downtown Chicago and this gave us a new perspective.

Response from Host, Jun 2025

We're so glad to hear you enjoyed the tour! Hope to see you for another one.

Chicago Gem

Debra_S, Apr 2025

Lots of great historical info on Chicago and beautiful area (S. Prairie Ave.) to walk around. Loved the Palmer House brownie at the end of the tour at the gorgeous Palmer House!

Response from Host, Apr 2025

Glad you enjoyed the tour!

Great Tour of the Prairie Ave. District, and much more. Important part of Chicago History!!!

Brian_M, Apr 2024

I've lived in Chicago/Chicagoland for 40+ years, and I always wanted a tour of the Prairie Ave. District. Much of the city's history - especially post-Civil War - is linked to this area. The tour did a great job of not only explaining the area, but also other important landmarks along the way (for example, Chess Records, Second Presbyterian Church, the Chicago Athletic Association, and the Palmer House). One of the remaining, original Prairie Ave. District mansions is Glessner House, and the tour here was excellent. BTW, the preservation of Glessner House is impeccable; they have done an excellent job preserving this home. The Prairie Ave. District tour includes a brief ride on the elevated train, which is something you should do while in Chicago. If you are new to Chicago, you are better off starting with a tour of the basics, like an architecture tour. But if you are a local, or a prior Chicago visitor, you should consider taking this tour to broaden your understanding of Chicago's important history.

Hidden gems!

Nicole_D, Oct 2023

Tom was a wealth of knowledge about Chicago. The meeting location at the Chicago Athletic Association was so cool. Beautiful building, as were the others on the tour. Enjoyed the lesson on riding the L. We had a great time and really enjoyed all the places we visited.

Recomended

Cecilia_H, Aug 2021

We like to know the history of cities we visit, and this tour gave us a glimpse of Chicago of the 1800s visiting homes, grand hotels and also simply strolling around places with a story. The tour guide was excellent.