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 in between the Federal Building Columns. 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
5.0
(63 Ratings)
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Sudarshanh2023
May 7, 2025
Recommend this👍🏻 - We had good time our guide Ben was very friendly and gave lot of information about all the buildings on the way would recommend to all
Review provided by Tripadvisor
Anna
Apr 20, 2025
Nice experience - Very interesting tour. The guide was very prepared and engaging. We learned many interesting things about the history and architecture of Chicago.
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Mcmdm1979
Apr 4, 2025
Chicago Architectural Tour - Mitchell delivered an engaging, well paced tour. The details offer great insight to the area history and development, Applying what we learned is keeping our eyes open as we explore more. A good experience!
Review provided by Tripadvisor
P1647liadelineb
Mar 30, 2025
Great. - Beautiful view the guide was very nice We learn the history of buildings I recommend this activity. The 2h passes very quickly it is really attractive as walk the guide is there a lot it gives life to the walk
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H2810dysantiagog
Feb 26, 2025
Really enjoyed and learned a lot with Dave - We really enjoyed and learned a lot of Chicago’s architecture with Dave. He seamed to know a lot, but mainly we felt that he enjoyed sharing his knowledge. As he said, if you don’t like architecture, you can’t be a tourist guide in Chicago. I loved the city and Dave reinforced this feeling.
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Cristicreme
Jan 21, 2025
Lark, you're a rockstar! - We had an amazing time on the tour! Our tour guide, Lark, was so knowledgeable about the architecture and also general history in Chicago. We asked lots of questions as a group, which in turn uncovered even more interesting facts and stories. Would definitely recommend. The timing was spot on, as well. Do note that where you begin is not where you end the tour, but the tour guide should be able to direct you where to go.
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G8921vsma_t_b
Jan 12, 2025
To do! - Great experience, with an interesting and open guide who shared his knowledge with great enthusiasm.
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345ervics
Dec 31, 2024
The Chicago Riverwalk Architecture Tour with Dave - Visiting Chicago from Atlanta, we decided to explore the city through its famous Riverwalk and booked a tour guided by Dave. Let me tell you, it was an unforgettable experience! Dave was an absolute gem of a guide. His passion for Chicago’s architecture was infectious, and his storytelling made the city’s history come alive. From iconic landmarks like Marina City to the towering Willis Tower, every building along the Riverwalk seemed to have a story, and Dave told each one with such clarity and enthusiasm that even someone with no background in architecture (like me!) could appreciate the artistry and history. The Riverwalk itself was stunning—a perfect blend of modern design and natural beauty. Walking along the river, surrounded by Chicago’s breathtaking skyline, was a feast for the senses. The mix of vibrant restaurants, quaint bridges, and serene water views made it feel like I was stepping into a postcard. Dave’s knowledge, humor, and approachable nature turned the tour into more than just a sightseeing trip—it was an experience that left me feeling connected to the city. If you’re visiting Chicago, I can’t recommend this tour enough. Thank you, Dave, for making our first Chicago adventure so memorable!
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605tb
Dec 27, 2024
Fascinating buildings and trends - Ben did an outstanding job. Architecture could be a dry subject but he brought fun and made history live. Thanks Ben. Terri and Harry Budow
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Laura
Dec 23, 2024
Amazing! - Dave was an exceptional guide! Despite the cold we had enjoyed the walk a lot and all the data and history it provided helped us to know more about the City, resolved all our doubts with a lot of kindness. Definitely amazing! I would recommend all my friends and family to take this tour with Dave
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).