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Prairie Ave Tour: Chicago's Historic Gems
5.0
24 Ratings
Chicago
Explore Chicago’s elite past on the Prairie Ave District Walking Tour. Visit historic mansions, iconic landmarks, and enjoy exclusive docent-led tours.
Explore Chicago’s elite past on the Prairie Ave District Walking Tour. Visit historic mansions, iconic landmarks, and enjoy exclusive docent-led tours.
Duration:
4 hours
Cancellation:
24 hours
Highlights
- Chicago Athletic Association - The Unbound Collection by Hyatt - Begin the adventure with a guided tour of this historic hotel. Next, proceed to Washington & Wabash to catch the Green line train heading to the Prairie District.
- Chess Records - Following a short walk from the Cermak L station, participants will discover the building that was…
- Chicago Athletic Association - The Unbound Collection by Hyatt - Begin the adventure with a guided tour of this historic hotel. Next, proceed to Washington & Wabash to catch the Green line train heading to the Prairie District.
- Chess Records - Following a short walk from the Cermak L station, participants will discover the building that was pivotal in producing some of Chicago’s most iconic and influential Blues music.
- Second Presbyterian Church of Chicago - Enjoy a private, docent-led mini tour.
- Spoke & Bird Cafe (South Loop) - Pause for a snack at this distinctive employee-owned and woman-owned cafe (purchases optional).
- Glessner House Museum - Experience a private, docent-led mini tour.
- Clarke House Museum - Visit the oldest house in Chicago and learn about the lifestyle of elite Chicagoans at the turn of the century.
- Palmer House Hilton Historic Lobby - After returning to the Loop by train, explore the stunning interior of this renowned building and conclude the tour with a delightful treat.
What's Included
- Transit tickets
- Church and Glessner House donation/fee
- Local expert guide
- Transit tickets
- Church and Glessner House donation/fee
- Local expert guide
What's Not Included
- Gratuities
- Food and beverages
- Gratuities
- Food and beverages
Additional Information
This exceptional tour of the Prairie Ave District is a must-see experience.
Discover how Chicago’s wealthiest citizens lived at the turn of the century and what remains today. This distinctive Chicago tour starts with a visit to one of the city’s newly-revitalized areas: the magnificent Chicago Athletic Association Hotel.
A brief journey on the Green…
This exceptional tour of the Prairie Ave District is a must-see experience.
Discover how Chicago’s wealthiest citizens lived at the turn of the century and what remains today. This distinctive Chicago tour starts with a visit to one of the city’s newly-revitalized areas: the magnificent Chicago Athletic Association Hotel.
A brief journey on the Green Line brings participants to the Prairie Ave District, which boasts numerous historic sites such as Motor Row, the former Chess Records, and the city’s oldest house. As the tour progresses along Prairie Ave, participants will enjoy views of historic mansions and a picturesque park. The tour’s highlights include TWO exclusive, docent-led mini tours at the national landmark Second Presbyterian Church (featuring many Tiffany windows) and the Glessner House. Additionally, there will be a mid-tour pause at a local employee-owned and woman-owned café. The tour concludes with a train ride back to the Loop for a final stop (and a delightful treat) at the elegant Palmer House Hotel.
- Should be able to climb stairs as not all train stations are equipped with elevators
Location
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.
For a full refund, cancel at least 24 hours before the scheduled departure time.
Customer Ratings
5.0
(24 Ratings)
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Teresa_b
Oct 4, 2025
Great tour of the Prairie District - 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.
Review provided by Viator
W340ugjc
Sep 28, 2025
Gilded Age Grandeur - Absolutely wonderful tour! From start to finish, it was a fantastic experience. The architecture was breathtaking, each building telling its own unique story, and I loved how every stop had such rich historical significance. Tom was incredibly knowledgeable, weaving together the past and present with engaging stories that really brought the whole tour to life. Whether you’re a local or a tourist, I’d highly recommend this tour. It’s an immersive journey that’s both informative and visually stunning!
Review provided by Tripadvisor
Q8264ujabigailk
Jun 28, 2025
Great tour - highly recommend!! - Tom was a great and passionate tour guide offering many unique stories along the way! Learned so much about a cool area in Chicago you don’t hear about often. It was also nice to stop by a variety of places to have more context throughout the tour. Would highly recommend!!
Review provided by Tripadvisor
Marla_a
Jun 22, 2025
A completely new Chicago perspective! - 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.
Review provided by Viator
Debra_s
Apr 13, 2025
Chicago Gem - 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!
Review provided by Viator
Eleanorc467
Oct 10, 2024
An Afternoon of Chicago History - I loved this tour! It was very informative and really interesting to learn about the mansions and the lives of the people who lived there. Tom is an excellent your guide. He's obviously steeped in knowledge and full of stories about the area. Tom is also friendly and very accommodating for us older folks! Thank you so much! I wrote an earlier review, but am not sure if went through sorry if this is a repeat!!
Review provided by Tripadvisor
Terrysh8171zx
Oct 2, 2024
Touring the city with a man who loves his hometown - Friends and I have been touring Chicago for the whole Spring and Summer, on our own, in the company of a group/docent, and this weekend, with a man who truly loves his native city and wants to share it with others. If you take an L Stop tour with Tom, you will learn many things and come away with a better understanding of what makes Chicago tick. He researches his topic and lovingly develops a tour which is factual and entertaining. Many other tours have been good, but our tour with Tom was exceptional. He met us on time and greeted us with warmth and kindness; he was prepared for the weather with rain ponchos if we needed them; he kept the group together and kept a pace that all could manage throughout the tour. He handled a few delays on the L with calm and patience. Aside from the fact that he is a competent manager of a tour group, Tom was exceptional for many other reasons. He knows the city and its gems and this tour reflected this. He was knowledgeable about the neighborhood we were touring, Prairie Avenue and the South Loop, sharing stories and insights and not just facts. He could answer any question often with a humorous anecdote. The tour is jam-packed with interesting history and stories of old Chicago. But the thing about this tour that sets it apart from other tours is that he made us feel the great pride in and love he has for the city of Chicago. As a native Chicagoan myself, and one who loves my city deeply, it was a wonderful experience to share it with a like-minded person and learn many new things. We would love to take more of the tours with L Stop Tours and experience again this gifted teacher. We'll see you soon, Tom.
Review provided by Tripadvisor
Yolandamm3209ey
Sep 8, 2024
This Tour is Well Worth It!! - I highly recommend this tour! The guide was great, loads of information, many interesting tidbits of Chicago history.
Review provided by Tripadvisor
Jls522
Aug 13, 2024
Great tour! - My husband and I thoroughly enjoyed this tour. We had never explored this part of the city before and Tom led our group around with ease. We covered a lot of ground during our 4 hour tour and there's still more to see. Tom is very knowledgeable about the city and can answer any question you may have. I highly recommend this company and we will tour with them again!
Review provided by Tripadvisor
Brian_m
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