Chicago Walking Tours

Chicago is one of the world’s great walking cities.  At L Stop Tours, we carefully design each of our tours to include a mix of Chicago’s famous sites and attractions — historic architecture, cultural venues and interesting places to enjoy food and drink.

Our tours are fun, engaging and provide a unique perspective of the city that you won’t find on other tours.  We go inside famous buildings, not just look at them from the river or the top of a double-decker bus. We visit pubs and restaurants that have great Chicago stories, not just establishments that are convenient to our route. We explore diverse neighborhoods throughout the city, learning about their history and culture. And, whenever possible, we take a ride on the L train, Chicago’s iconic public transit system. L Stop Tours offers experiences that are perfect for both tourists and locals.

L Stop Tours has been called one of the most unique Chicago neighborhood tours in the city by Choose Chicago, the official destination marketing organization for the city.

Ready to find the tour that’s right for you? Explore all of our Chicago tours!

 
 
 
 
 
 
 
 
 
 
 
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 Wendy J 
 
19 July 2025
 
 
  
Tom was an excellent tour guide as we went underground to the Pedway.  We enjoyed seeing some Tiffany and other stained glass work and how to get to those sites while avoiding the brutal sun & heat. We were so happy to be in the AC as it was around 90 while visiting Chicago.  We shared what we learned with a friend that wasn't able to join us and he'll use the pedway when he's in town for work.
  
 
 
 
 
 
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 John Chapman-Rienstra 
 
12 July 2025
 
 
  
We went on the "Prairie Ave District" walking tour, and really enjoyed it! The tour started at the Chicago Athletic Association (which is now a hotel), which has a fascinating history and architecture -- well worth another visit on your own! We then took the Green Line down to the area around Prairie Ave, and stopped by a couple other historic sites (e.g., Chess Records) and visited Second Presbyterian Church, which has breathtaking stained-glass windows. From there, we walked to Prairie Ave and had a tour of the Glessner House. The mansion and the stories about the family were fascinating. We walked past some of the other historic homes on Prairie Ave and spent some time in the Chicago Women's Park (although the Clarke-Ford House is temporarily closed), then walked by Motor Row and then went back to the Loop, ending at the Palmer House Hotel (and had one of their famous brownies!). Tom was a wonderful guide -- very knowledgeable and charming. I learned a ton about each place we went on the tour -- well worth the time and money!
  
 
 
 
 
 
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 Missi Grove 
 
22 May 2025
 
 
  
I really enjoyed the Chicago Pedway tour with Tom. It’s a great way to see a different side of the city—especially if you’re looking for something a little off the beaten path. The Pedway itself is full of interesting history and hidden architecture, and Tom did a great job bringing it all to life. He’s clearly very knowledgeable and shared lots of fun facts and stories along the way. The tour was well-paced, easy to follow, and perfect for escaping the weather while still seeing parts of downtown you’d probably miss otherwise. Highly recommend if you’re curious about Chicago’s underground side or just want a unique walking tour experience.
  
 
 
 
 
 
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 Karolina Antonina 
 
11 May 2025
 
 
  
2 weeks ago we attended a Friday underground Chicago tour. The idea of Chicago pedway is a great one and so is the tourguide Tom who is a very patient and extremelly knowledgable person. We do recommend Tom and his tours, and we do regret we couldn't participate in his other tours.
  
 
 
 
 
 
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 Mollie Brice 
 
3 May 2025
 
 
  
We enjoyed our tour very much! It was just my husband and me and our guide was so accommodating and took us to a few extra sites because we had time! He had great info to share along the way for additional places for us to check out too.  Highly recommend for a city tour from a unique perspective.