Let's make it easy: What are you looking for?


I have lived in the Chicago suburbs for most of my life and I love going into Chicago to enjoy our beautiful city. Still, I have learned more about Chicago’s architecture this past year than in all the others combined. Hillary crafts her tours to tell a story, which I just love.
— TripAdvisor reviewer, October 2016

Click the image for a montage of photos from our tours!

Inside Chicago Walking Tours is a top walking tour company founded by an experienced tour guide and product development director for a major sightseeing company in Chicago. Given the freedom to research and construct her own tours, she used her experience as a teacher, writer, improv comedian, and tour guide to create tours that tell the story of Chicago in an engaging, educational, and always entertaining way. Inside Chicago Walking Tours combines architecture, history, and storytelling in one powerful experience of the city that no other tour company can match.

Unlike tour companies who rely on gimmicks or giveaways to convince you to take their tours, we trust Chicago and our way of presenting it to be worthwhile enough without needing to bribe customers to try us out.  Simply put, you won't get snacks or prizes on our tours because we don't need to sweeten our tours with such things. Chicago is one of the most beautiful cities in the world, and that's enough for us, period.

What makes us different? It's our ability to find the hidden and fascinating details of buildings and areas that people pass through or pass by every day. It's our emphasis on experiencing architecture as an art, appreciating both the exteriors and interiors of Chicago's gorgeous buildings. It's our passion for showing visitors, whether they be out-of-towners or Chicagoans, a side of Chicago that they haven't noticed before: the second side of the Second City.

Photo by Ed McDonough, @digucator

My family has been on many walking tours across the US and around the world, and this was by far the best.
— TripAdvisor reviewer, May 2016
This was an amazing experience. I have done a few tours in Chicago, but this is the one I will always remember.
— TripAdvisor reviewer, September 2016

Private & Group Tours are always available...

In addition to our regular public tour offerings, we offer private tours all season long.  Tours are priced on a flat-rate basis depending mainly on the size of the group.  Contact us here to start planning!