All-Weather Chicago History & Architecture Trek

Event Category


Event Overview

Have you lived in Chicago for years but have never played tourist in your own town? Are you hosting family and looking for something fun to do? Just visiting for a few days? Spend 2 hours trekking through the city with me and you'll be blown away at all the history and architecture Chicago has to offer. I'll take you to see some of Chicago's prominent sights like The Chicago Theatre, City Hall, Daley Center, and Plaza, Picasso Statue, Marina Towers, Riverwalk, Wrigley Building, Millenium Park and Cultural Center as well as a few things that are off-the-beaten-path. We'll learn what makes us The City That Works as well as some great stories about how things came to be.

We'll meet in a popular sheltered spot to discuss the tour and begin our way trekking through Chicago. I'll guide us through some of the underground Pedway system that is known to only a percentage of Chicagoans (we have 5 miles of Pedway!). We'll learn about the history of The Windy City (as well as why we're REALLY called The Windy City) while popping outside to see some of our city's most prominent sights. Using some of the Loop's sculptures and overhangs, we'll get rare, unique views and traverse the city like a local while staying warm and dry. For an additional perspective, we'll jump into some buildings to admire the architecture and art. Be prepared for indoor and outdoor walking as some of our walks and views will take us outside, especially if the weather is pleasant. Layers are recommended during the colder/rainier months. Please let me know if you have any allergies or food sensitivities, as we’ll be stopping for an authentic Chicago snack that's been around for decades. Whether you're a local or this is your first visit, I promise to pack lots of interesting tidbits into our 2 hours together!

COVID-19 UPDATE: We're spending more time outside as there is PLENTY to see & keeping the groups small so we can practice safe social distancing. I will be wearing a mask and will ask that everyone in the group wear one as well. I have disinfecting wipes too. P

Whether you're a local or this is your first visit, I promise to pack lots of interesting tidbits into our 2 hours together!

Minimum age

All ages welcome

What's Provided

Rain ponchos, if neededSnack

Cancellation Policy

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I'm Kelly (a.k.a. ChiCitiGirl), a mapgeek, history enthusiast, architecture admirerer and food fanatic. I'm a trained city guide (5star tours!) and I've been doing excursions for friends & family for decades. The Windy City has been my home for 25+ years and I know how to get around to experience the best sights and bites. Working in the food and beverage industry for 10+ years has given me added insight into some of Chicago's hottest spots. I'm also a Chicago Artictecture Center Open House volunteer and Chicago History Museum member, using their library to research Chicago as well as the history of the 125+ year Victorian building I call home. I've traveled the world doing walking tours and know from personal experience how to make the best of our time together. I try to make a new friend every day, come play with me!

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