Best Skyscraper Tours: Our Top 7

1.Chicago Premium Driving Tour with River Boat Cruise and Sky Deck

★★★★★★★★★★4.5 · 165 reviews · 4 hours (approx.) Our pick

In about four hours, you’ll see Cloud Gate, cruise past more than 40 architectural landmarks, stop at Buckingham Fountain and the Adler viewpoint, and ride between sights with a local guide such as Tony, Robert, or Joe. Downtown pickup and drop-off make this a handy first look at Chicago.

“Danny was very knowledgeable about Chicago. Gave us plenty of time to look around at each stop. Well worth the money. Thanks Danny.”

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2.Chicago Walking Tour: Art Deco Skyscrapers Loop

★★★★★★★★★★5.0 · 138 reviews · from $35Best value

Walk Chicago’s Loop with a Chicago Architecture Center-certified guide and spot Art Deco details at 30 N LaSalle, the Rookery, 135 S LaSalle, 1 N LaSalle, and the Board of Trade. The 90-minute tour includes selected building interiors and gallery admission at the Architecture Center.

“Look up and see what you are missing. Chicago is graced with many beautiful buildings and the fine details of the Art Deco structures abound in downtown.”

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3.Florence Skyline from the Top of Brunelleschi’s Dome

★★★★★★★★★★4.5 · 99 reviews · 2 hours 30 minutes (approx.) · from $106

Explore Florence’s Duomo area with a local guide, then climb Brunelleschi’s Dome independently. Your pass also covers the cathedral, baptistery, Opera del Duomo Museum, and Giotto’s Bell Tower for 72 hours. Guides including Claudio and Maurizio are praised for clear, lively explanations.

“Great guide , very knowledgeable and fun group. Overall, amazing walk through of the city up until the climb to the Duomo at sunset.”

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4.Chicago Walking Tour: Historic Skyscrapers

★★★★★★★★★★5.0 · 67 reviews · from $35

Join a Chicago Architecture Center certified guide for a 90-minute walk through the Loop’s landmark skyscrapers. See the Fine Arts Building, Auditorium Building, Rookery, Board of Trade, Marquette, and Monadnock, then use your included gallery admission at the Architecture Center.

“Excellent! Our tour guide, Angela Platt, was wonderful. She had a lot of knowledge about all of the buildings. We learned things about the different styles of architecture and she took us in the buildings and pointed out the inside and the styles inside. I would highly recommend this tour.”

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5.Chicago Walking Tour: Art Deco Skyscrapers Riverfront

★★★★★★★★★★5.0 · 53 reviews · from $35

Meet a certified Chicago Architecture Center guide for a 90-minute walk from the riverfront to The MART. You’ll see five Art Deco landmarks, enter several grand lobbies when open, and hear stories from guides such as Ron Roman, Mitch, Betsy, and Cynthia. Groups are capped at 15.

“This is a wonderful walking tour. We visited a lot of landmarks like the Mart and the carbon and carbide building. Our guide, Ron Roman, was approachable, professional, and above all knowledgeable. We learn so much from the tour. ArchitRead more”

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6.Walking Tour: Chicago’s Loop – Home of the Modern Skyscraper

★★★★★★★★★★5.0 · 36 reviews · from $65

Spend about three and a half hours with a local guide such as Tom, walking through Chicago’s Loop and riding the L train. See early skyscrapers, manual elevators, landmark interiors, Macy’s tiled dome, and the Chicago Cultural Center’s enormous Tiffany dome in a group capped at ten.

“Absolutely loved this tour. Tom is a great tour guide and knows and loves his city. Learned so much about Chicago and its buildings. Real highlight is getting inside the buildings and seeing some of the most amazing architecture. You can walk through Macy's and not see the incredible tiled dome, just look up.”

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7.Chicago: Art Deco Skyscrapers Walking Tour

★★★★★★★★★★4.8 · 28 reviews · 1h 30m

Meet your Chicago Architecture Center docent at 30 N LaSalle Street for a 90-minute, small-group walk through five Art Deco skyscraper lobbies. Learn to spot sunbursts, zigzags, octagons, and lavish materials while visiting landmarks near the Chicago River. Admission to the Center’s exhibits is included.

“Very good experience and the pace and knowledge shared was very good and informative”

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