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
(80 Ratings)
5 stars
4 stars
3 stars
2 stars
1 star
Carla_t
Dec 6, 2025
Excellent tour with Ben.... - Excellent tour with Ben. Better than expected. He was knowledgeable, informative and very entertaining. We covered a lot of ground and it was a wonderful mix of history, architectural sites , beautiful landmarks and holiday decor. Highly recommend.
Review provided by Viator
Sancarlostraveller
Nov 14, 2025
Architecture along the Magnificent Mile - The tour was mostly centered around the architecture of the many fabulous buildings along the Magnificent Mile. We had also done a boat tour, also highly recommended, but with the walking tour you are able to see the buildings up close, and stop and see how the different styles fit together to make downtown Chicago so unique. Our guide, Ben, was a wealth of information and gave great context to what we were seeing.
Review provided by Tripadvisor
Andrew
Nov 12, 2025
Brilliant tour - Ben was absolutely brilliant from start to finish.Very informative and kept us entertained throughout the entire tour with his enthusiasm and humour
Review provided by Tripadvisor
Getaway44285666201
Oct 25, 2025
Great tour guide ! - Ben was fun to walk around and a great tour guide felt like hanging out with a good friend showing me his city great experience!
Review provided by Tripadvisor
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
From $39
up to 15 guests
1 - Adult
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).