Chicago Skyline Tour: Architecture Highlights

Discover the iconic architecture and landmarks that have shaped Chicago on a captivating walking tour along the Chicago River. Immerse yourself in the city’s history and legacy with our expert guides.

Duration: 2 hours
Cancellation: 24 hours
Highlights
  • Millennium Park - Begin your tour at the Federal Building Columns and delve into the history of Chicago’s lakefront. Then, explore the Italian Renaissance style at the nearby Chicago Cultural Center.
  • Chicago Riverwalk - Enjoy the stunning Beaux Arts and Art Deco architecture along the water, featuring three iconic Chicago buildings from the…
What's Included
  • Professional local guide
  • Guided walking tour of Michigan Avenue
  • 360 Chicago ticket (if you upgrade)
  • Visits to Rush Street, Millennium Park, and more
What's Not Included
  • Gratuities
  • TILT (can be purchased on-site)
Additional Information

Discover the narrative of Chicago through its skyline on a walking tour that spans from the city’s 19th-century origins to its most impressive contemporary towers. This architecture tour encompasses everything from Beaux-Arts to modernist to Art Deco styles.
Begin near the stunning Millennium Park to take in the lakefront vistas. Then, follow your guide…

Location
Federal Building Columns
East Randolph Service Street
Meet your guide on the north side of the Cancer Survivors’ Garden in front of the Federal Building Columns (corner of Field Boulevard and E. Randolph Street). Your guide will be wearing an orange hat that says ExperienceFirst.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.9
(79 Ratings)
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Cathy_g
Oct 18, 2025
Engaging tour - Ben was great, full of enjoyable, light hearted and informative. Very helpful with Chicago suggestions too.
Review provided by Viator
49carlosa
Sep 10, 2025
This tour is a MUST - Ben was awesome. This tour is highly recommended. Definitively, a great opción of you look for a bite of history of Chicago
Review provided by Tripadvisor
Salc509
Sep 5, 2025
Historical Chicago Buildings Tour - Ben was great and very informative. He provided a historical review of Chicago’s amazing history beginning pre-fire to present. Then he showed us various historical buildings, and shared about their history and some of Chicago’s influential figures from the past.
Review provided by Tripadvisor
Terrilk2022
Aug 20, 2025
A great experience! - Lark was extremely knowledgeable about the buildings along the tour, as well as curious about questions that were asked. There was a great mix of stops and walking to mix up the two hours. I am not one for heavy or intense guided tours as I like to go am my own pace... but Lark was very open about making the experience accessible for all interests. I learned so much about key buildings in Chicago, and I feel that the knowledge is already enhancing my enjoyment of the rest of the trip. Thank you Lark!
Review provided by Tripadvisor
Camper55907840687
Aug 17, 2025
Ben the magnificent tour guide. - Ben was an excellent guide who was very knowledgable about the city history, the culture, and the architecture. He took us through the magnificent mile which included many high end stores. I recommend this tour to anybody who would like to know more about the city. Thanks Ben for a memorable experience.
Review provided by Tripadvisor
Stw2021
Aug 17, 2025
Great tour of architecture at Mag Mile - The tour with Ben was very interesting and made very exciting with many little stories. Highly recommended!
Review provided by Tripadvisor
Maria_c
Aug 15, 2025
Ben our tour guide, was... - Ben our tour guide, was very knowledgeable and I loved his presentation. He kept the tour interesting, with a bit of humor.
Review provided by Viator
Artccc12
Aug 15, 2025
Good walking tour - Very Interesting tour around Downtown buildings and Chicago architecture. 2 mile walking. Good tour guide Ben tells interesting stories and facts from the Chicago history.
Review provided by Tripadvisor
Marcelgj6857jo
Aug 14, 2025
Insightful and Entertaining - Much to learn in a short amount of time. Ben was a fantastic Tour guide and covered a lot of stuff in 2 hours. Very chill and casual. Highly recommended !
Review provided by Tripadvisor
Ashleybg9010di
Aug 6, 2025
Magnificent Mile Tour - Ben was so informative of the city and answered all the questions my group and I had! He even sent a thorough follow up email with additional recommendations of what to do in the city for our weekend stay which was very helpful as well!
Review provided by Tripadvisor
From $39
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).