Prairie Ave District Tour: Chicago's Historic Gems

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 - Meet your guide and kick things off with a tour of this historic hotel. Then we’ll head to Washington & Wabash to board the Green line train to the Prairie District.
  • Chess Records - After a brief stroll from the Cermak L station, guests will learn about the building that…
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….

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.

Customer Ratings
5.0
(19 Ratings)
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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
436bobz
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
Cynthiaee
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
H8155rznicoled
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
Nicole_d
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
Derl98
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
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