What To Expect

What‘s Included

Reviews

• Great tour of the Prairie District

  Teresa B,,Oct 4, 2025

  - Review from Viator

  5.00

  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.

  

• Gilded Age Grandeur

  W340UGjc,,Sep 28, 2025

  - Review from Tripadvisor

  5.00

  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!

  

  

  

  

  

  

• Great tour - highly recommend!!

  Q8264UJabigailk,,Jun 28, 2025

  - Review from Tripadvisor

  5.00

  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!!

  

  

  

  

  

• A completely new Chicago perspective!

  Marla A,,Jun 22, 2025

  - Review from Viator

  5.00

  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.

• Chicago Gem

  Debra S,,Apr 13, 2025

  - Review from Viator

  5.00

  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!

• An Afternoon of Chicago History

  eleanorc467,,Oct 10, 2024

  - Review from Tripadvisor

  5.00

  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!!

• Touring the city with a man who loves his hometown

  terrysH8171ZX,,Oct 2, 2024

  - Review from Tripadvisor

  5.00

  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.

• This Tour is Well Worth It!!

  yolandamM3209EY,,Sep 8, 2024

  - Review from Tripadvisor

  5.00

  I highly recommend this tour! The guide was great, loads of information, many interesting tidbits of Chicago history.

• Great tour!

  jls522,,Aug 13, 2024

  - Review from Tripadvisor

  5.00

  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!

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

  Brian M,,Apr 10, 2024

  - Review from Viator

  5.00

  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.

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