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 at 10:30AM

Saturdays at 1:00PM  – (Starting on 11/5/16, the Saturday Pedway Tour will move to a 10:30AM time slot.)

The tour is 90 minutes and is 20$ per person.


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 The Fairmont Hotel – 200 N. Columbus – come inside the lobby and I’ll meet you there in my fancy red baseball cap.

FINISH: Tours end roughly at Michigan and Randolph

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


The BADASS Winter Tour – Starts 12/1/16

The Winter Tour

I LOVE WINTER!!! I’m totally serious, I really do. It’s pretty and quiet and the steel gray of the sky and the steel gray of the buildings and it’s all just so cool and strong and Chicago. And there’s something to going out on a long, brisk, winter walk and then coming inside, rosy-cheeked, getting warm, rubbing hands, sipping tea…

So! I have created a Winter Tour that is all of things I love about the cold, come enjoy winter with me!! Pull on your long-underwear and your warmest undershirts, pile on the cozy sweaters and scarves, zipper up your coat, snap on your mittens and join me on this urban winter wonderland walk.

We’ll head out to see trippy Maggie Daley Park and it’s “why didn’t we think of that before” skating ribbon! Then we’ll head to Millennium Park to check out The Bean (SO cute with a lil pat of snow on the top!) then a lovely heated break as we get ready to head to Lake Michigan! The lake is so pretty in winter and calm and strong and scary and peaceful – it’s just beautiful and it’s a whole different lake than it’s sparkling summer counterpart.

There will be “warming” breaks here and there, but I’m going to be honest with you here, we will not be turning back for cold! Please see this link on What To Wear In Winter In Chicago. No messing around with this stuff, it is important that you give a Chicago winter the respect it deserves. This tour is not for the slightly dressed.

The Winter Tour

**If it is dangerously cold outside, your lovely tour guide will take care of you. We’re still going outside, but we’ll do a lot more warm breaks and the path of the tour may change a bit, but that is only under very extreme conditions. Not much will scare away us away.

Tour Times

Thursdays 1:00-2:30

Fridays 4:00-5:30pm
Saturdays 1:00-2:30pm
Sundays: 9:00-10:30am

Tour Prices

The Winter Tour is $25 per person.

What to expect

Cold. Expect it to be cold.

Long underwear
Lots of layers
*Better to have too much than too little*



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!

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 1:00-2:30pm
Fridays 3:00-4:30pm
Sundays: 1:00 – 2:30PM

Tour Prices

The In The Loop Tour is $20 per person.

START: Harold Washington Library – 400 S. State

FINISH: State and Randolph-ish

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 Disaster! Tour

The Disaster! Tour

“If there’s a flaw, it’s human. It always is.” Colin Farrel – Minority Report

What do a dense army captain, an unbalanced boat and mess of ghost cows have in common? They’re all included on the Disaster! Tour. Come with me as we talk about Chicago’s greatest disasters (the Chicago fire isn’t even close to our biggest disaster in terms of lives lost!) and alternately, some of it’s greatest victories. I have sad disasters, big ones, little ones and just to make sure I don’t lose you completely, I even have some funny ones.

We’ll traipse through the Loop, up and over, down and under, no part of the urban fabric is free from mayhem! And honestly, we probably laugh and have more fun on this tour than any other – so if you’re sensitive – you should still come! This is such a great way to learn about this resilient city and I do cow impressions. So…

Tour Times

Starting 9/25/16 The DISASTER TOUR will also run Sundays at 10:30AM

Fridays at 1:00PM

Tour Prices

$20.00 per guest.

What to expect

This tour is about a mile of walking and we move fast! City streets, curbs, noise and all of the above are to be expected. This tour is great for kids if they’re not too sensitive, but I never take it too far. Heh.

Start: NW Corner of Wacker & Wabash in front of the George Washington (and friends!) statue

Finish: Clark Street and The Chicago River


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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