"Easily the best walking tour of Chicago."

(TripAdvisor review)


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Why "Inside" Chicago? 

Because we go inside at least a few beautiful, fascinating buildings on EVERY TOUR!

Check out our 2018 tours...

My family has been on many walking tours across the US and around the world, and this was by far the best.
— TripAdvisor reviewer
We are regular visitors to Chicago and this is hands down the best tour we have experienced.
— TripAdvisor reviewer

Our tours at a glance:  What can you expect?

  • You will go INSIDE a handful of buildings on nearly every route (The Time Traveler's Tour is the only exception), and the buildings are unique to each route;
  • Your tour will last 2 hours, and cover one and a half miles at a very leisurely pace;
  • You will stay within the fascinating and historical center of the city (the Loop and River North), within easy distance of most hotels;
  • You will learn about architecture and history in a highly dynamic, engaging, and context-based way that sticks with you;
  • You'll be given great opportunities for photos that are very different from what most tourists get;
  • You'll enjoy tours that are ALL created by Hillary, company founder and head tour guide, based on her own exploration of the city and her never-ending (and very nerdy) research.  She is extremely passionate about showing you Chicago like you've never seen it!

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.

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

Private & Group Tours

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!