Prairie Ave District: Historic Chicago Walking Tour
15 Ratings
Duration: 4 hours
Cancellation: 1 day learn more
  • Begin your journey with an introduction from your tour guide and a visit around the historic lodge. Subsequently, we’ll get to Washington & Wabash to take the Green line train to Prairie District.
  • Upon a short walk from the Cermak L station, attendees will gain insight about the establishment that produced some of the most noteworthy and influential Blues tunes of Chicago.
  • Attendees will have a private tour guided by a knowledgeable docent.
  • Pause for a while and relish a bite at this distinctive cafe operated and owned by employees and women (buying is optional).
  • Attendees will have a private tour guided by a knowledgeable docent.
  • Attendees will witness the most ancient dwelling in Chicago and comprehend how high-class Chicago inhabitants led their lives during the beginning of the century.
  • Following our return train journey to the Loop, we’ll investigate the exquisite inner part of this renowned building and conclude the tour with a delectable delicacy.
What's Included
  • Transit tickets
  • Church and Glessner House donation/fee
  • Local expert guide
What's Not Included
  • Gratuities
  • Food and beverages
Additional Information

This exceptional exploration of the Prairie Ave District is a must-see.

Experience the lifestyle of Chicago’s richest denizens during the turn of the century and witness its remnants today. This distinct Chicago exploration commences with a discovery of one of the city’s recently rejuvenated locations: The magnificent Chicago Athletic Association Hotel.

A quick journey on the Green Line transports us to the Prairie Ave District, a locale with numerous historical landmarks such as Motor Row, the erstwhile Chess Records, and the city’s oldest dwelling. As we amble down Prairie Ave, we are greeted by historical manors and a picturesque park. The tour’s main attractions, nonetheless, are TWO intimate, docent-guided mini tours at the national landmark Second Presbyterian Church (known for its numerous Tiffany windows) and the Glessner House. We’ll also pause midway at a locally owned/female-owned cafe. Subsequently, we re-board the train back to the Loop for our final destination (and a delightful sweet) at the refined Palmer House Hotel.

  • Should be able to climb stairs as not all train stations are equipped with elevators
Chicago Athletic Association - The Unbound Collection by Hyatt
South Michigan Avenue
Find your guide inside lobby, immediately to left
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
(15 Ratings)
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1 star
Apr 10, 2024
Great Tour of the Prairie Ave. District, and much more. Important part of Chicago History!!! - 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.
Review provided by Viator
Nov 5, 2023
Unique Tour! - Unique tour! I have lived in the Chicago area for most of my life, yet I learned so much about Chicago I never knew. Tom, our tour guide was enjoyably terrific! Great historical perspective - he even brings his iPad to show us vintage pics demonstrating before vs. current. One highlight that sticks out: we visited 2nd Presbyterian Church and saw 9 amazing refurbished Tiffany stained-glass windows. Not a dull moment. :-)
Review provided by Tripadvisor
Nov 4, 2023
A Great Tour - Tom was amazing. He was so knowledgeable and friendly. My sister and I want to take a personal “Under Chicago” maybe in the spring. Tim is me of the best tour guides I’ve met
Review provided by Tripadvisor
Oct 2, 2023
Hidden gems! - Tom's tour was lovely. We enjoyed all the sites, hidden gems, and history stories! Such a wonderful time to spend the day. The meeting location and learning to ride the L were super fun too!
Review provided by Tripadvisor
Oct 1, 2023
Hidden gems! - 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.
Review provided by Viator
Jul 4, 2023
Fantastic tour of Prairie Avenue District - We have found our L Stop tours to be much more in-depth than others we have taken. All while keeping them interesting and entertaining. We very much like the size of Tom’s tours. This really feels almost like a personal tour as opposed to being herded like cattle in a large group. We appreciate that we can hear the tour guide when he is talking instead of being at the back of large group trying to listen. We learned so much about the Prairie Avenue neighborhood. The two stops for mini docent led tours were a nice addition. (Though the docent at the church did not seem to know the details I might have expected about the Tiffany windows we were there to look at.) Riding on the L is always interesting and a good start for this tour. Tom does a great job mixing up the walking with a stop to explain something and then letting us explore on our own for a bit (in the Women’s Park) and then allowing time to sit down for a refreshment. This tour was fun, interesting, thorough while not being rushed. Great tour!
Review provided by Tripadvisor
Aug 23, 2021
Recomended - 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.
Review provided by Viator
Aug 16, 2021
A walk around the neighborhood - It was a beautiful day to walk around the neighborhood enjoying the architecture, and the cuisine of the area. Our guide was very knowledgeable and easy to communicate with.
Review provided by Tripadvisor
Sep 26, 2019
A new adventure! - We did this tour this week to explore an area of the city that we did not know with somebody who did - and had a wonderful time. Tom has a whole lot of knowledge and mixes walking the neighborhood (narrating fun facts along the way) with mini-tours, public transportation and even food along the way... all taken care of ahead of time so we could just enjoy. We will be certain to not only recommend LStop Tours to others but to take in a few of their other neighborhood tours as well ~ a great day!
Review provided by Tripadvisor
Sep 17, 2019
A better way to see Chicago! - We did the Prairie District green line tour on a Saturday. It's a fantastic way to see parts of the city that perhaps many people overlook. (At least we had!) It was just Tom and the two of us, and we loved every minute! We've lived in the greater area our whole lives, and I always thought I had a pretty good working knowledge of the city. If you make the effort to look around other areas and allow someone to tell you about these places, you just might be amazed at what you didn't know. I certainly was. If you're like me, always exploring and trying to learn new things, then this is something you should experience!
Review provided by Tripadvisor
Select Date and Tickets
minimum 2 guests
up to 10 guests
July 2024