Skip to content

From Architecture to Food in Chicago

Chicago, United States

Check local COVID-19 restrictions before booking

Experience hosted by David

5 hours
Includes food
Up to 9 people
Hosted in English

What you'll do

We start our tour under the dazzling marquee of the Chicago Theater, where you might recognize the neon sign from the movie musical Chicago. We then head off into the bustling city, where our first stop is inside one of the best-preserved spaces built for shopping in Chicago, featuring an unforgettable atrium at its core.

We then head toward the Chicago Pedway, a unique feature of Chicago used by locals and commuters daily to move about the city in a network of underground tunnels. We head back above-ground near City Hall, and on most weekdays, we’re able to head inside to see the classic interior design and architecture.

From there, we hop on either the “L” train or a water taxi on the Chicago River (depending on the weather and time of year). Both options offer a uniquely local Chicago experience! Once we’re back on solid ground, we make our way to another delicious destination for locally made chocolates from a Chicago staple.

Your food tour starts with a very well-known Chicago fare: the Chicago-style hot dog. Every Chicagoan has his or her own preference as to how the dog should be made, and you get a chance to try your guide’s favorite version.

After you’ve filled up on pizza and hot dogs, we take a stroll through two more establishments, each one essential to Chicago’s food culture. We then continue our tasting journey with a classic Chicago sandwich: Italian beef.
Other things to note
Dress standard: Please dress comfortably, casually, and in weather-appropriate attire. Wear comfortable shoes for walking.

Closure of sites: In the event of road or attraction closures, your guide will do their best to work around the obstacles or take your tour to alternate locations.
We start our tour under the dazzling marquee of the Chicago Theater, where you might recognize the neon sign from the movie musical Chicago. We then head off into the bustling city, where our first stop is inside one of the best-preserved spaces built for shopping in Chicago, featuring an unforgettable atrium at its core.

We then head toward the Chicago Pedway, a unique feature of Chicago used by locals and commuters daily to move abou…

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
    A variety of food samples (such as a Chicago-style hot dog, deep dish pizza...
From $54
/ person
Wed, Jan 27
10:00 AM - 3:00 PM
$67 per person
$67 per person
Sat, Jan 30
10:00 AM - 3:00 PM
$67 per person
$67 per person
Mon, Feb 1
10:00 AM - 3:00 PM
$67 per person
$67 per person

Meet your host, David

Host on Airbnb since 2019
  • 6 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

Ready to discover some of the best Chicago has to offer with a local by your side? Join us on an epic tour of some of the city’s greatest hits: incredible architecture both old and new, delicious local treats and iconic Chicago dishes, a uniquely Chicago transit ride, stunning river views, and much more!

Rated 5.0 out of 5 from 6 reviews.

Tracey
November 2020
We had the most AMAZING tour with our guide Wallach. He brought the city to life with his knowledge of the history, landmarks, and culture of Chicago. He was so kind, attentive, and personable. I highly recommend the tour and if you’re lucky enough to have Wallach as your guide... you are in for a real treat!!! Tracey and Becky
We had the most AMAZING tour with our guide Wallach. He brought the city to life with his knowledge of the history, landmarks, and culture of Chicago. He was so kind, attentive, an…
Cassandra
October 2020
The experience was great! The places we went to eat were one of a kind. I felt like I could get around the city after leaving the Tour.
Pamela
October 2020
Wallach was amazing! He knew things about the city even locals can overlook. I felt safe and left with a deep sense of what this city has to offer. If you’re ever in town, please book the architecture AND food tour. Trust me, it’s soo worth it. Thank you, Wallach!
Wallach was amazing! He knew things about the city even locals can overlook. I felt safe and left with a deep sense of what this city has to offer. If you’re ever in town, please b…
Jack
September 2020
This is a combination of a architecture walking tour and local food tour. My guide ( David) grows up in the area and is very passionate about his hometown. We had a great time! The Italian beef sandwich and deep dish pizza are the best i have ever had!
This is a combination of a architecture walking tour and local food tour. My guide ( David) grows up in the area and is very passionate about his hometown. We had a great time!…
Myracle
December 2020
Wallach is a great tour guide 👍
Thu
December 2020
Wallach is really knowledgeable about the city. I had a good time with this tour. The food portion is large and delicious.

Choose from available dates

24 available
1 / 2

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.