Chicago Walking Tours

If you’re looking for the best in Chicago walking tours, then you have come to the right place! Please peruse the offerings and if you have any questions, feel free to ask! If you are interested in a custom or private tour, just let me know. I like doing them. I’ll rock it out for you.

Reservations are required for all Chicago walking tours: You can either purchase tickets on the website, or you can call me 773.593.4873 or write me at margaret(at)

The Chicago Pedway Tour

Mondays & Thursdays
Monday/Thursday Pedway Tour
Saturday Pedway Tour

Monday, Thursday at 10:30 and Saturday at 1:00PM  – 90 minutes – 20$

Your first question may be – what the heck is the Pedway anyway?

And my answer would be, the Pedway (along with Lower Wacker IMHO) is the unsung hero of Chicago.

Sure, some may see only shoe-shine places and convenience stores, but we know better!  When we start to dig into the Pedway and examine it – it reveals itself to be a fascinating study.

The Pedway is a series of walkways that run above and below (mostly below)  buildings in the Loop it’s not a well-known part of the city, a mystery to even the most seasoned natives. It will challenge your logic, your senses (it mostly smells pretty good, I promise!) and definitely your sense of direction. There’s art and beauty and life down there,  and the best part is, you are basically getting a full Chicago highlights tour without ever going outside! So good.

START: The Monday/Thursday tour starts at The Thompson Center – 100 W. Randolph – come inside and head DOWN the escalator and meet me in the dead center of the food court. I’ll be in my fancy red baseball cap.

The Saturday Pedway Tour starts at Block 37 Mall at 108 N. State between Randolph and Washington.

FINISH: Monday/Thursday ends at Randolph & Michigan. Saturday tour ends at Michigan & Wacker.

EXPECTATIONS: About a mile and a half, good amount of walking, ups and downs and escalators, etc.



The In The Loop Tour

The “In The Loop” Tour is everything you want to know about Chicago all rolled into one fabulous walking tour. It’s a architecture! History! Pretty things! Stories of cows, fires, egos and artists!

This is the perfect Chicago walking tour if this is your first time here or need a primer before the rest of your stay. It’s also a great tour for locals to help us remember just how awesome this city truly is. I give a lot of different kinds of information on this tour and I’ll show you how it all comes together. Plus, we laugh a lot, so.

We’ll start our Loop tour with some skyscraper history, we’re pretty proud (you think?) and I’ll tell you why. We’ll ogle at early skyscrapers and their modernist brothers.  We’ll see Tiffany glass lobbies and find the love for Mrs. O’Leary’s cow. We’ll head to the prettiest hotel lobby in the city and learn about the “popular” kids of old-timey Chicago. We’ll talk about the elevated train, why it’s called the Loop and help you get your bearings. We’ll peer out at the busy city from hidden vantage points others don’t know about and I’ll fill you in on our sordid and magical history.

It’s a passion tour, it’s all the things that make me love this city. I want to share them with you, wandering around the Loop on a sunshiny day is how it’s supposed to be.

Tour Times

Thursdays 1:00-3:00pm
Fridays 3:00-4:00pm
Sundays: 1:00 – 3:00PM

Tour Prices

The In The Loop Tour is $25 per person.

What to expect

We will be traversing city streets, curbs, crowds and fun! There might be escalators, stairs, etc. This tour goes rain or shine, please dress accordingly!


THE FOLLOWING TOURS ARE AVAILABLE FOR PRIVATE TOURS OR BY APPOINTMENT ONLY! I’m fun by appointment only, which really just means, “private tour.”A private tour can be as little as one or two people (it’s a 75$ minimum!) so it’s not fancy, unless you want it to be fancy!


BINOCULARS TOUR (Everyone gets a pair of binoculars and we’re looking at gargoyles, etc!)







Fresh off the success of a Second City tour, the 12-year improv vet who’s “done funny” at the Playground, iO and Annoyance, among others, says she’ll break into impersonations, which include urban planner Daniel Burnham, the late Mayor Richard J. Daley (who, she added, “sounds remarkably similar to Junior”) and Bertha Palmer. – Time Out Chicago

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