"Hillary and the tour were dazzling, amazing, and full of wonderful surprises. She has created one of the most enjoyable, beautiful and unique tours we have ever taken."

TripAdvisor review


What makes Inside Chicago Walking Tours different from other tour companies?


It's all about the tour guide, and this one is simply awesome. 
She has a diverse background in teaching, entertaining, and performing, as well as substantial experience in researching, creating, and leading architecture tours of Chicago, both boat tours on the river and lake, and walking tours on land, and was head of product development for a major boat tour company in Chicago.  Hillary added one very specially chosen and highly trained guide to her company's roster in 2017, and another one in 2019. Adam and Ian are highly engaging, knowledgeable, and eager to teach about Chicago!


Our guides don't use  or need  a script or notes.  Period.
Think about it: it's not a very good sign when your tour guide — the person who's supposed to really know what they're talking about — reads you information from a notebook or script given to them by their boss.  Many tour groups in Chicago are led by guides who do just that: the majority are well-meaning, unpaid volunteers whose guests are at the mercy of their training for that particular tour route.  Want to know more outside of that particular route?  Sorry, buddy: it's not in the script.  And honestly, you can tell when a script has just been memorized, and no one likes that.  


We'll tell you real stories, not just a forgettable laundry list of facts. 
We know that the best way to get information to "stick" with people — and to be interesting to people — is to convey it like a story, with a logical beginning, middle, and end.  Most architecture tours of Chicago — boats, walks, segways, etc. — present you the city like an overwhelming laundry list of information that you'll likely forget.  For us, there is a reason we are exploring a certain area, or following a certain path: the architecture that we explore is like the vocabulary of the larger story we are telling.


You get to see Chicago's architecture inside and out.
Though a boat tour is a wonderful way to see Chicago, it has a few drawbacks:  big crowds, no personal interaction with your guide, and — especially — you only see the exteriors of buildings! For this reason, on our architecture walking tours, we love to focus on the fantastic and often under-appreciated interiors of buildings throughout downtown Chicago — including many of the buildings along the river.  We even provide you with an "insider's scoop" on lots of the exterior architectural elements that most guides won't show you.


We have proof that our way of presenting the city is highly effective.
The original inspiration for starting this architecture walking tour company came over the course of your guide's tenure as an architecture tour guide on the Chicago River:  often at the end of her tours, people would ask her how they could take another tour with her specifically — a tour of anything in Chicago, as long as it was with her. Realizing that her way of presenting the city was so captivating for people, she knew she was onto something, so she decided to "follow the fun," as they say in improv comedy.


We make up our own rules and style.
Our architecture walking tours are created not according to any particular company's existing "style" or parameters, but rather, they are created purely — 100% — according to what we find to be the most interesting and worthwhile things to see in central Chicago in a short amount of time.  Period.  These walking tours showcase what we truly enjoy about this city, and they show you Chicago as only someone who truly knows it and loves it can.


We don't need to rely on battery-operated gimmicks and free prizes to make our tours interesting.

Here's an analogy:  you go to a steakhouse, and you order a steak.  You assume the steak will stand on its own as the star, without needing extra bells and whistles.  Your server brings it out, along with sparkly garnish, candles, and a Mariachi band to distract you while you're eating.  Kind of trying too hard to convince you to like their product, aren't they?  Just like the stand-alone star steak, our tours stand alone:  it never even occurred to us to bribe tour guests with free food, cheap prizes, battery-operated whatevers, and various shareable technology or notebooks that you have to give back at the end of the tour.  It's a walking tour: do you really need all those gimmicks if it's a really good tour?  Shouldn't it just stand on its own as the star?  Yeah, we think so too.




(872) 529-2523


Downtown Chicago
Various tour locations

Call Center Hours

24/7 (if no answer, please leave message)


Different routes running daily starting at 11am, 12pm, 1pm, 2pm, and 3pm (see Tour Calendar for specific info).


Tuesdays, Wednesdays, and Thursdays:  Please contact us to book private tours for your group (see rates here).

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