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All-Weather Architecture & History Trek

Chicago, United States

Check local COVID-19 restrictions before booking

Experience hosted by Kelly

2 hours
Includes food, equipment
Up to 10 people
Hosted in English

What you'll do

I pack lots of sights, sounds and experience in this tour so put on your walking shoes! We first meet in a sheltered spot to discuss the tour and begin our way trekking through Chicago. We'll use the expansive city sidewalks, plazas, parks and Riverwalk as well as part 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 digesting some of our city's most prominent sights. Using some of the Loop's buildings and sculptures, we'll get rare, unique views and traverse the city like a local. If you're curious about Prohibition-era ganster lore or our speakeasy past, we can cover that too. Be prepared for indoor and outdoor walking as our trek will take us outside, especially during Covid for fresh air. 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 a century where they also serve the city's best hot chocolate with an extra punch. 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 have disinfecting wipes too
I pack lots of sights, sounds and experience in this tour so put on your walking shoes! We first meet in a sheltered spot to discuss the tour and begin our way trekking through Chicago. We'll use the expansive city sidewalks, plazas, parks and Riverwalk as well as part 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'r…

Kelly's commitment to safety

This host committed to Airbnb’s COVID-19-related safety and cleaning guidelines—including adhering to social distancing guidelines, practicing good hygiene, and ensuring that all participants wear a mask.
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What's included

  • Food
    We'll sample a local snack from a decades-old Chicago staple
  • Equipment
    I'll provide a rain poncho, should you need one
From $29
/ person
Sat, Jan 23
3:30 PM - 5:30 PM
Join 2 other guests
$29 per person
$29 per person
Sun, Jan 24
3:30 PM - 5:30 PM
Join 1 other guest
$29 per person
$29 per person
Tue, Jan 26
11:30 AM - 1:30 PM
$29 per person
$29 per person

Meet your host, Kelly

Host on Airbnb since 2014
  • 78 Reviews
  • Identity verified
I'm Kelly (a.k.a. ChiCitiGirl), a mapgeek, history enthusiast, architecture admirerer and food fanatic. I'm a trained city guide (5-star tours!) and I've been doing fun excursions for friends & family for decades. The Windy City has been my home for 26 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 Architecture Center Open House volunteer, river kayak guide & Chicago History Museum member, using their library to research Chicago as well as the deets 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!
I'm Kelly (a.k.a. ChiCitiGirl), a mapgeek, history enthusiast, architecture admirerer and food fanatic. I'm a trained city guide (5-star tours!) and I've been doing fun excursions for friends & family for decades. The Windy City has been my home for 26 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 Architecture Center Open House…
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Where you'll be

I'll take you to see some of Chicago's prominent sights like The Chicago Theatre, Picasso Statue, City Hall, Daley Center and Plaza, Marina Towers, Riverwalk, Wrigley Building, Millenium Park and Cultural Center as well as a few things that are off-the-beaten-path. We'll view some some stunning interiors and artwork, all while learning what makes us The City That Works as well as some great stories about how things came to be.

Rated 5.0 out of 5 from 78 reviews.

Jessica
December 2020
Kelly is great! She told us stories of the city’s history, took us to some great photo ops. and have awesome food recommendations.
Dillon
October 2020
AMAZING!!! My first Airbnb experience was so worth the money. I was hesitant about it but Kelly was so personable, friendly and knowledge about the city. You can tell she really enjoyed teaching me about Chicago and its architecture. It was a little cold and rainy, but I didn't mind at all as she is a great storyteller and I leaned 1000x more about Chicago than I would have on my own. Kelly absolutely sold me on the Airbnb experience!
AMAZING!!! My first Airbnb experience was so worth the money. I was hesitant about it but Kelly was so personable, friendly and knowledge about the city. You can tell she really en…
Elisabeth
October 2020
Kelly is an excellent guide and we learned a lot. We were happy with the small group size and everyone wore their masks.
Jordan
October 2020
Kelly's tour was everything we were hoping for! She provided such great information and presented in such a friendly welcoming way. We felt as if a good friend was giving us a walk around the city explaining things we never would have known about otherwise. A tremendous value. I highly recommend a tour with Kelly, hands down! Thanks Kelly!
Kelly's tour was everything we were hoping for! She provided such great information and presented in such a friendly welcoming way. We felt as if a good friend was giving us a walk…
Carol
October 2020
Excellent tour. We only had one day to discover Chicago, so Kelly’s tour was a great way to learn a lot in a short period of time. Very glad we signed up.
Liselle
September 2020
Kelly was absolutely amazing ! She’s knowledgeable, patient and welcoming. The tour took us to some great picture perfect spots. If you’re a history buff, appreciate architecture or just want to get to know the city in a short amount of time this tour for you.
Kelly was absolutely amazing ! She’s knowledgeable, patient and welcoming. The tour took us to some great picture perfect spots. If you’re a history buff, appreciate architecture o…

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Things to know

Cancellation policy

Any experience can be canceled and fully refunded within 24 hours of purchase, or at least 7 days before the experience starts.

Guest requirements

Up to 10 guests ages 6 and up can attend.

What to bring

Please be prepared for the weather as we will be inside and out. Layers are recommended. Comfortable shoes are a must.