Chicago Walking and Train Tours

Discover Food, Culture and History Via the L System

We Explore Chicago and Its Neighborhoods

At L Stop Tours, we believe you haven’t seen Chicago until you’ve explored the Loop and many of our city’s vibrant neighborhoods. From historic areas such as the Prairie Avenue District to the colorful street murals and delicious cuisine on our Pilsen neighborhood adventure, L Stop Tours offers experiences that are perfect for both tourists and locals.

Our tours are fun, engaging and provide a perspective of the city you don’t get from other Chicago walking tours. We ride the train to diverse neighborhoods and explore interesting sites in the vicinity of L stops.

Our Chicago walking and train tours are a different way for friends and family to see the very best of our beautiful city. L Stop Tours has been called one of the most unique Chicago neighborhood tours in the city by Choose Chicago!

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

What Makes Us Different

We include an expert local guide and transit fees (if applicable) in the price of every tour, in addition to fees/donations for churches, museums, etc. Food and beverages are purchased by guests.
We keep our Chicago walking tours small (max 8 people) to ensure a more intimate experience.
Our tour guides are knowledgeable, experienced, and engaging.
We ride the L on most tours, enabling us to easily visit a variety of Chicago neighborhoods.
We walk to historic sites and local establishments that are located close to L stations.
We keep it interesting and fun! We’ll tell you good stories but we won’t overload you with long lectures and memorized facts.

Read our TripAdvisor Reviews

Google Reviews

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

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

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

2021-10-31

Tom was great. He would have continued even longer had we not tired of rain.

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

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

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

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

2020-03-09

We do tours every time we travel. this was more than we expected.

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.