Chicago Walking Tours

Hi! I’m so pleased you’re here. I love this city and I may be a small business in the scheme of things, but I’m a really good tour guide and I love it and I love sharing it with you! Yay! I’ve had my own tour business for seven years, been a tour guide for ten and I’m proud of my Certificate of Excellence from Trip Advisor. I like to keep my tour groups small so we can enjoy our tour together and you won’t get lost in the shuffle.

Check out the tours and if you have any questions, please ask! I also do private tours, student groups and corporate outings, give me a call if you’re interested.

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

(The Saturday Pedway Tour will go on hiatus for the season on May 20th. If you want more Pedway this summer, check out the Monday/Thursday Pedway Tour or Chicago Mix Tour! )

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

And my answer would be, the Pedway (along with Lower Wacker IMHO) is the unsung hero of Chicago. It’s an all-indoor series of hallways and walkways that keep Chicago warm (and cool in the summer!) and dry.

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. This tour will talk about the Pedway, the history of it and how to use it, but you also get a really great insight into the city, it’s architecture and it’s history. Plus, we have a ton of fun on the Pedway Tour.

The Pedway is 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 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.

Buy Pedway Tour Tix

Tour Info:

These 90-minute tours are 23$ per guest.

Monday & Thursday at 10:30AM Start: The Thompson Center

Saturday 10:30AM Start: The Fairmont Hotel


Pedway Tours at State and Randolph

The Chicago Mix Tour


So ok, you’re looking through the tour offerings and you’re thinking, well, The Pedway Tour sounds weird and cool but I would also like to be outside, see beautiful buildings and Beans….

Peanut butter and chocolate!

The Chicago Mix Tour is the best of all possible worlds – a little bit country, a little bit rock ‘n roll. We’ll see Chicago from the inside for an hour, then we’ll head outside for an hour. It’s everything you asked for, it’s having cake and eating it, it’s like Christmas and your birthday all rolled into one.

On the all-indoor, Chicago Pedway portion, we’ll see Marshall Fields (some may call it Macy’s ahem, we’ll talk about it) and my favorite building in the whole city, the Cultural Center! I will pry you away from the largest Tiffany dome and we will go the SUPER SECRET way to Millennium Park.

In Millennium Park we’ll see the Bean and Gehry’s Pritzer Pavilion and we’ll cross the crazy snake bridge (the views are bananas) to Maggie Daley Park, a truly trippy and awesome kids park. From there I’ll tell you the saddest story ever (I know, but it’s a great story) and we’ll end the tour near the gift shop of the Art Institute.

This is a lovely tour, a quirky tour and most importantly, an informative tour. We cover a lot of ground (above and below!) and we see a lot of the city! Plus, it’s a GORGEOUS tour, lots of Tiffany glass and steel and lakes. Great for photographers!

Tour Info

Fridays at 10:30AM and  Saturdays at 1:00PM.

This two-hour tour is 30$ per guest.

Tour Start: Block 37 Shopping Mall – 108 N. State    Finish: Michigan & Randolph

The Disaster! Tour

What do a dense army captain, an unbalanced boat (ship, it’s a ship, stop calling it a boat Margaret) and a mess of ghost cows have in common? They’re all included on the award-winning Disaster Tour! Come with me as we talk about Chicago’s greatest disasters (the Chicago fire doesn’t even come close to our biggest disaster in terms of lives lost!) and alternately, some of it’s greatest victories. Sure, it might feel weird to learn about a city this way, but Chicago is strongest when it’s mettle is tested. 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! What I love about this tour is it takes us to all kinds of different locations. And honestly? We laugh and have a ton of fun on this tour – so if you’re sensitive – you should still come! Finally, this is a great way to learn about Chicago’s “can do” attitude, why we’re so proud of what we’ve overcome, AND, I do cow impressions, so, you wouldn’t want to miss that.

Buy Disaster! Tour Tix

Tour Info:

Thursdays and Sundays at 1:00PM

This two-hour tour is $30.00 per guest.

Start: The Cultural Center – 78 E. Washington Finish: Clark Street and The Chicago River

The Binoculars Tour

The Binoculars Tour will change the way you look at the buildings around you forever. I mean that too. ForEVAH!!! And not just while you’re in the city, but this will change the way you look at buildings at home too. Impress your friends with your architectural knowledge!

This downtown Loop tour focuses on learning how to “read” a building by understanding the ornament on it’s facade. Building ornament may be useless – structurally useless – but it is not arbitrary! In fact, it’s full of deep meaning and conveys a message to all who see it, but the trick is, you have to see it.

SO! Like a gaggle of campers, each of us armed with a pair of binoculars (that you get to keep), and a hilarious and knowledgeable tour guide (you have to give me back), we’ll set out to explore where no one else does. We’ll see griffins, demons and gargoyles!

We’ll “read” some of Chicago’s best buildings, like the Chicago Board of Trade, the Rookery and the Chicago Temple (it’s a skyscraper church, it is cool and it has some seriously scary and sad ornament on it). Grab your binoculars, lean against a building and look up, see the beauty and the artistry that most people today never, ever see.

Buy Binoculars Tour Tix

Tour Info:

Fridays at 3:00PM

This is a 90-minute tour and is 28$ per guest (this includes your binoculars of course!

Start: Chicago Board of Trade  Finish: Daley Plaza – 50 W. Washington

The EarlyBird Tour

We morning people know that the best time to see anything is before everyone else is even awake. This holds true for Chicago and it’s gorgeous parks! On this lovely tour, we’ll start out by walking to the lake to catch the sunrise or pretty darn close to it. That magic light shines over Chicago’s skyline, it’s so quiet and gorgeous. Then we’ll cross through Maggie Daley Park – Chicago’s newest and trippiest park.

Then over to Millennium Park to see the Bean in peace! It’ll smell so fresh and dewey over there, you won’t believe it. On this tour we’ll learn about Chicago architecture and why oh why we love steel so very much. We’ll drink tea and coffee and talk art and Beans and wives of the mayors.

This is such a great and inspiring way to start your morning (it is for me too, I love this tour!), you’ll feel like a million bucks and your photographs will be beautiful!

Grab a coffee and a donut and come meet me for the prettiest of all my tours! You won’t regret it. I promise.

Buy EarlyBird Tour Tix

Tour Info

Sundays at 7AM

This 90-minute tour is 23$ per guest.

Start: Fairmont Hotel       Finish: Fairmont Hotel



Private tours are my specialty. If you’re looking for something specific or have an idea, I can totally help! If you’d like me to put something excellent together for you, I’d love to, we can talk and I’ll find out what you’re interests are and we can plan a private tour for the ages! I’ll give you the straight scoop too, not just the standard take on the standard information.

Prices for a 90-minute private Chicago walking tour are 30$ per person and a 90$ minimum, so if it’s one, two or three people, it will be 90$! If you’d like a longer tour, let me know and we can work that out as well. (Private tour prices are seasonal).

Groups over 8 people, give me a call or shoot me an email and we can talk price and length, etc. Private tours are a great way to get exactly what you want out of your walking tour, so please feel free to email me at margaret(at) or call me at 773.593.4873. Fun!





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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