Chicago Architecture & Highlights Tour

Chicago, Illinois, United States

Experience hosted by David

  1. 2.5 hours
  2. Hosted in English

What you'll do

We start at the Chicago Theater before heading off into the city. We’ll begin by exploring the Chicago Pedway. This network of tunnels and bridges connects skyscrapers and retail stores, so you’ll see how locals move around the city (especially during those Midwestern winters)! We’ll then make our way past City Hall, where you'll get a chance to enjoy the beauty of the historical architecture while your guide shares about its history.

You can’t visit Chicago and not see some incredible public art, so next, we’ll stop at the Picasso Sculpture (yes! A real Picasso!). You’ll hear how this piece came to Chicago and how it was received, as you enjoy an up-close Picasso experience with this unique piece of art. Weather permitting (aka, in the warmer months), we’ll then take a stroll along the Chicago Riverwalk while taking in views of several soaring buildings, such as the Wrigley Building and Tribune Tower.

Finally, we’ll walk down the world-famous shopping district of Chicago’s Magnificent Mile, making our way to the beautiful lakefront parks along Michigan Avenue. At some point, your guide will serve up a delicious local treat for you to enjoy. We’ll end up in the picturesque Millennium Park, home to the iconic Bean sculpture, where your tour ends.

If you would like to book this tour for a private group, please message us directly for more information.
We start at the Chicago Theater before heading off into the city. We’ll begin by exploring the Chicago Pedway. This network of tunnels and bridges connects skyscrapers and retail stores, so you’ll see how locals move around the city (especially during those Midwestern winters)! We’ll then make our way past City Hall, where you'll get a chance to enjoy the beauty of the historical architecture while your guide shares about its history.

What's included

  • Food
    A surprise local treat!

Meet your Host, David

Host on Airbnb since 2019
  • 245 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 North America Tour Hub, a nationwide 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!
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 North America Tour Hub, a nationwide 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 a…
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From $32/ person

$39 per person
$39 per person
Join 2 other guests
$39 per person

Where you'll be

The tour takes place downtown, one of the most exciting areas in Chicago. We'll go past some beautiful buildings, we'll go underground to the Pedway, and we'll experience some unique Chicago public art. We'll also stroll down the iconic Magnificent Mile and enjoy exploring the beautiful lakefront parks along Michigan Avenue, ending up in Millenium Park with the iconic Bean sculpture.

Rated 4.90 out of 5 from 245 reviews.

Haines
October 2021
David was a great guide. He was super enthusiastic and had a lot of fun facts and interesting tidbits about the city. Would highly recommend. It was a great way to spend the day.
Kat
October 2021
We had Kevin as our tour guide and just loved his energy for history and for Chicago! He was very interactive with the group and personalized it for us with the plans with had for the day. Definitely would recommend this tour if you’re wanting to know more about the history of Chicago and the architecture!
Ali
October 2021
Kelly was a great tour guide! Obviously super knowledgeable about Chicago and made sure to get to all the must do’s Chicago has to offer. Definitely would recommend to all ages!
Jason
October 2021
We had a wonderful time on our Chicago history tour with Kelli. She did a wonderful job, was extremely knowledgeable about Chicago history, and helped us re-discover the city after being gone from it so long. The tour covered a number of important sites around the loop and the Chicago River area. I would recommend this especially as an orientation to the city. It was also great to be back with people touring after such a long hiatus.
Ana
September 2021
David is a incredible guide that has amazing facts about the city. As he makes us walk around the downtown area we learned about history, music, city myths, fun facts and even get to grab a bite of some of the “musts” of Chicago. We had a good time!
Stephanie
September 2021
Great tour! Wallach was super knowledgeable! Always wanted to come to Chicago and glad I got a taste of the history, great people, & food as well!

Choose from available dates

10 available
1 of 2 pages
  • Sun, Dec 5
    4:00 PM - 6:30 PM
    $39 per person
  • Mon, Dec 6
    9:30 AM - 12:00 PM
    $39 per person
  • Mon, Dec 6
    4:00 PM - 6:30 PM
    Join 2 other guests
    $39 per person
  • Wed, Dec 8
    9:30 AM - 12:00 PM
    $39 per person
  • Wed, Dec 8
    4:00 PM - 6:30 PM
    $39 per person
  • Thu, Dec 9
    9:30 AM - 12:00 PM
    $39 per person
  • Fri, Dec 10
    9:30 AM - 12:00 PM
    $39 per person
  • Fri, Dec 10
    4:00 PM - 6:30 PM
    $39 per person

Things to know

Cancellation policy

Cancel up to 7 days before the Experience start time for a full refund, or within 24 hours of booking as long as the booking is made more than 48 hours before the start time.

Guest requirements

Up to 10 guests of all ages can attend.