We heard the river cruise was a definite must for Chicago, but I say [this] walking tour by far blows it out of the water. In fact, my friend and I thought it was underwhelming after what we had seen with Hillary.
— TripAdvisor reviewer, July 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

This was without a doubt the absolute best walking tour I have ever been on.
— TripAdvisor reviewer, March 2016
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

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!


We did a plethora of touristy venues in Chicago over a 3-day visit and we all agreed this was by far the highlight of our trip.
— TripAdvisor reviewer, March 2016
We were looking for a new experience in Chicago because we go there often and have done all the traditional things. Inside Chicago was exactly what we were looking for.
— TripAdvisor reviewer, May 2016
This isn’t just someone spouting a script and then moving on. Hillary clearly lives and breathes local history, and ebulliently shares her natural curiosity for what’s behind everything we see and experience in everyday city life.
— Yelp reviewer, September 2015