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Chicago Culture and Architecture Tour

Chicago, United States

Check local COVID-19 restrictions before booking

Experience hosted by David

2.5 hours
Includes food, transportation
Up to 9 people
Hosted in English

What you'll do

We start at the Chicago Theater before heading off into the city. Our first stop is one of the best-preserved spaces in Chicago, featuring an unforgettable atrium. We’ll then make our way to the Chicago Pedway: an underground network of tunnels used by locals daily - especially during the Midwest winters.

We then head to City Hall and, on most weekdays, head inside to see the classic interior design and architecture. Next, we’ll get to share a sweet treat: Chicago-style popcorn. Weather permitting, we’ll take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings.

From there, we’ll either hop on the ‘L’ train or a water taxi on the Chicago River (depending on the weather and time of year). Either option offers a uniquely Chicago experience! Once you’re back on solid ground, we’ll make our way to another delicious destination, enjoying views of the world-famous Wrigley Building along the way. Your second tasty confection is a locally-made chocolate!

Finally, we’ll take a stroll through the beautiful lakefront parks along Michigan Avenue. We’ll end up in the picturesque Millennium Park, home to the iconic Bean sculpture, where your tour ends.
Other things to note
This tour runs rain or shine, so please dress appropriately for the weather.
Personal shopping, additional food and drinks, and gratuity are not included.
We start at the Chicago Theater before heading off into the city. Our first stop is one of the best-preserved spaces in Chicago, featuring an unforgettable atrium. We’ll then make our way to the Chicago Pedway: an underground network of tunnels used by locals daily - especially during the Midwest winters.

We then head to City Hall and, on most weekdays, head inside to see the classic interior design and architecture. Next, we’ll get t…

David'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.
Learn more

What's included

  • Food
    Popcorn tasting, chocolate tasting.
  • Transportation
    Water taxi or "L" ticket.
From $35
/ person
Wed, Jan 27
10:00 AM - 12:30 PM
$43 per person
$43 per person
Sat, Jan 30
10:00 AM - 12:30 PM
$43 per person
$43 per person
Mon, Feb 1
10:00 AM - 12:30 PM
$43 per person
$43 per person

Meet your host, David

Host on Airbnb since 2019
  • 209 Reviews
  • Identity verified
We have a deep love and appreciation for the beauty, architecture, and unique culture of Chicago. Sharing our love for the Windy City with visitors (first-timers and frequent visitors alike) is a passion of Urban Adventures, a worldwide network of tour hubs. We are working alongside Airbnb to share our tours that focus on the local experience through the eyes of a native. Whichever tour you choose to take, you can be sure that you'll receive personal attention from a real, Chicago local and a unique experience that you'll never forget! Join us!
Co-hosts:
To protect your payment, never transfer money or communicate outside of the Airbnb website or app. Learn more

Where you'll be

The tour takes place downtown, one of the most exciting areas in Chicago. We'll go past, but also inside, some beautiful buildings (which most visitors don't do), we'll go underground to the Pedway, and we'll hop on either the "L" train or a water taxi. We'll also head to two Chicago staples and sample local treats. We'll end up in the beautiful lakefront parks along Michigan Avenue.

Rated 4.94 out of 5 from 209 reviews.

Justus
January 2021
Make sure to do this early in your trip. It will help you orient yourself in the city and show you where the best best places are to go. My tour guide Kelly was super helpful and really knew what she was talking about. Great introduction to the city!
Make sure to do this early in your trip. It will help you orient yourself in the city and show you where the best best places are to go. My tour guide Kelly was super helpful and r…
Daniela
December 2020
Wallach was incredibly knowledgeable and he made us feel super comfortable and safe, he kept a safe distance and wore his mask as well as provided sanitizer for us. The tour was awesome, this is our first time in a Chicago and it was so great being able to see all the historical landmarks and get to know this new place through the eyes of someone who has lived here his whole life, he had pictures that showcased just how much the city has changed over the years and also provided many interesting facts, we are definitely coming back and hope to do another tour when we do!
Wallach was incredibly knowledgeable and he made us feel super comfortable and safe, he kept a safe distance and wore his mask as well as provided sanitizer for us. The tour was a…
Jonathan
December 2020
I loved this tour. Everyday items you would easily miss is brought out and expounded on, showing the deep and rich culture and history of Chicago. Kelly was amazing, so knowledgeable, passionate, and hilarious. This is highly recommended. Thank you for the amazing time!!!
I loved this tour. Everyday items you would easily miss is brought out and expounded on, showing the deep and rich culture and history of Chicago. Kelly was amazing, so knowledgeab…
Jen
November 2020
My boyfriend and I decided to do a walking tour of Chicago while visiting, since we are both not very familiar with the city. Wallach was our tour guide and he did an excellent job of taking us around the city and explaining the history and significance of each stop. He was born and raised in Chicago, so he really knows his stuff! At the end, he even took us to a Chicago chocolatier and bought us all some candy :) Overall, great tour and I would highly recommend it!
My boyfriend and I decided to do a walking tour of Chicago while visiting, since we are both not very familiar with the city. Wallach was our tour guide and he did an excellent job…
Mustafa
November 2020
Awesome tour. David was an expert and showed us a really good time. Much needed if it’s your fist time in this beautiful city !
Kevin
November 2020
I had Wallach as my tour guide, and he was awesome! Really great to hear stories about the different buildings that you see in Chicagos skyline as well as a ton of other cool facts about the city. Was a great introduction to Chicago and Wallach went the extra mile in helping to guide everyone in our tour to our next destinations while giving some bonus facts.
I had Wallach as my tour guide, and he was awesome! Really great to hear stories about the different buildings that you see in Chicagos skyline as well as a ton of other cool facts…

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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 9 guests of all ages can attend.