Chicago Walking Tours

Discover the City's Culture, History and More

We Explore Chicago and Its Neighborhoods

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. And we explore diverse neighborhoods throughout the city, learning about their history and culture. 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!

What Makes Us Different

  • Owner of the company and lead tour guide, Tom, is a lifelong Chicagoan with a wide range of knowledge and personal experiences about the city.
  • We keep it interesting and fun! We’ll tell you good stories but we won’t overload you with long lectures and memorized facts.
  • We keep our public walking tours small (max 10 people) to ensure a more intimate experience.
  • We also offer customized private tours for larger groups.
  • Transit fees (if applicable) are included in the price of the tour. Some tours include a short train ride.
  • Our tours cover more ground and last longer than other walking tours but are timed so that you won’t lose interest or tire out.

Google Reviews

Alisa T. Weinstein
Alisa T. Weinstein
2022-01-25
I simply CANNOT say enough wonderful things about L Stop Tours -- our experience was utterly perfect and I happily recommend them to anyone visiting or even living in the Chicago area -- I guarantee you'll discover new gems in a city you think you already know well!
Beth Hamly
Beth Hamly
2021-11-15
The L Stop Tours are a fantastic way to see Chicago in a different way. Tom was extremely knowledgeable, personable and above all - FUN! Would be thrilled to do another of their tours on my next visit.
Jane Willig
Jane Willig
2021-11-03
We learned so much about Chicago architecture from our tour with Tom. . . .a true professional and a great value.
G J H
G J H
2021-10-31
Tom was great. He would have continued even longer had we not tired of rain.
Renee Shimizu
Renee Shimizu
2021-10-05
The tour itself was the perfect blend of indoors, outdoors and a ride on the L-train. From gawking at the incredible facades to exploring the insides of buildings we wouldn’t have normally thought to enter, the tour was engaging and entertaining. To top it all off, we learned how Frango’s got their name, as well as the difference between a food court and a food hall. But more than anything, it was Tom’s humor, love and knowledge of the city’s history that made this the best tour we’ve taken. A big thanks to Tom for showing us S. Fifth Avenue and making this our best trip to the Second City (take this tour and you’ll learn the origin of Chicago’s nickname too).
Matthew Smetana
Matthew Smetana
2021-09-21
We had a great tour of the Loop: Home of the Modern Skyscrapers. The tour took is in and out of a bunch of buildings. We had my parents along who are in their early 70's and my father is not used to that much walking but was still able to complete the tour no problem because of stops at the different building and elevators in most of the buildings. We would recommend this to anyone interested in history or architecture. The guide Tom was great and next time we are in Chicago would definitely look into another tour the company offers.
Chris Berno
Chris Berno
2021-06-15
We’re new to Chicago and took the Loop Modern Skyscraper tour. Our guide, Tom, lead us on a hands on experience that gave us an appreciation for the rich architectural history of the city and the origin of the L. And we learned a few of the city’s secrets along the way.
Dave Penning
Dave Penning
2021-06-10
Very knowledgeable host. It gives you a great incite into the history and beauty of buildings you normally just walk by.
Scott Thornton
Scott Thornton
2020-03-09
We do tours every time we travel. this was more than we expected.
Laurel Moad
Laurel Moad
2019-12-14
Green Line tour... What a treat to spend time in a neighborhood with an illustrious past. Our walking guide Tom shared a wealth of information about the history of the landmarks and antidotes of the area we visited. Starting the tour with conversation and coffee in the Chicago Athletic Association dining room was great way to break the ice. The docents at the 2nd Presbyterian Church and the Glessner House were fabulous! LOVED the original Tiffany windows at the church. The pace throughout the tour was perfect. Thank you Tom I look forward to scheduling other L-Stop Tours later this summer.

From the L Stop Blog