Best Skyscraper Tours: Our Top 15

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 $35Top rated

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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8.3-Hour Shanghai Bund Swift Tour with River Cruise or Skyscraper

★★★★★★★★★★5.0 · 26 reviews · from $112

You’ll tour the Bund with a private guide, then choose a 50-minute Huangpu River cruise or a visit to Shanghai Tower. Hotel pickup and drop-off, flexible start times, and guides such as Alana, Mary, Berlin, and Queena make this a useful choice for short Shanghai stays.

“The tour is well organized. As soon as I booked it, Alana reached out to verify hotel location for pick up and provided information of the tour guide. I’m traveling with my dad, who is 81 years old. Tour guide Ms. Mary and the driver Mr. Jin weRead more”

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9.Midtown Manhattan: Times Square & Skyscrapers Walking Tour

★★★★★★★★★★5.0 · 18 reviews · 2 hours (approx.) · from $25

Walk Midtown Manhattan in a small group of up to 15 people with an English-speaking guide. In two hours, you’ll connect Times Square, Bryant Park, the New York Public Library, Chrysler Building, Grand Central Terminal, St. Patrick’s Cathedral, and Rockefeller Center.

“Excellent! Our tour guide, Hans, exceeded our expectations. He was knowledgeable and personable.We actually toured for 3.5 hrs and the flew by.”

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10.The Story Behind NY’s Evolving Skyline An Architectural Journey Through History

★★★★★★★★★★5.0 · 18 reviews

Join Kitt Garrett for an on-demand architectural journey from Castle Clinton to Hudson Yards. Learn to spot New York’s major building styles, understand zoning and air rights, and use the downloadable PDF to explore the city at your own pace.

“Kitt is very methodical and organized in her narrative tour of NYC and it's architecture. I thoroughly enjoyed her detailed descriptions and locations of each structure and the reason for it's particular choice. It provided a true history of the great Read more”

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11.NYC Midtown Manhattan Times Square & Skyscraper Walking Tour

★★★★★★★★★★5.0 · 11 reviews · from $49

Spend two hours with an English-speaking licensed guide walking about one mile through Midtown Manhattan. See Times Square, Bryant Park, the New York Public Library, Grand Central Terminal, St. Patrick’s Cathedral, and Rockefeller Center, with a close look at skyscraper design and the city’s building race.

“This tour and the guide was excellent and took us to some really cool spots in Midtown Manhattan. It was a fun and educational experience. We all had a good time.”

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12.Chicago: Evolution of the Skyscraper Walking Tour

★★★★★★★★★★4.9 · 10 reviews · 1h 30m

Follow Chicago’s architectural story in building-by-building order, from river commerce and post-fire rebuilding to modern towers. Your English-speaking Chicago Architecture Center guide, possibly Mitch, explains the engineering, styles, and people behind landmarks such as the Page Brothers Building, Carbide and Carbon Building, and NBC Tower.

“Draws an informative connection between architecture, and people all in a compelling historic narrative of Chicago.”

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13.Chicago Loop: Art, Skyscrapers, Millennium Park & “The Bean”

★★★★★★★★★★5.0 · 6 reviews · from $49

Walk Chicago’s Loop with a local English-speaking guide, from Macy’s former Marshall Field’s building and Picasso to Millennium Park, Crown Fountain, Route 66, the Art Institute, and Cloud Gate. Expect two hours of architecture, public art, city history, and weather-friendly indoor stops.

“This tour was fantastic! Our guide was extremely knowledgeable and shared interesting stories about the city's history and the places we visited. The pace was just right. It was a great way to see the city and appreciate its architecture!”

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14.Chicago’s Modern Skyscrapers Guided Walking Tour

★★★★★★★★★★5.0 · 6 reviews · 1h 30m

Spend 90 minutes with a Chicago Architecture Center docent exploring Modernist landmarks along the Chicago River. See Marina City, the Daley Center, IBM Building, and Reliance Building, then visit the Center’s new exhibits. The tour runs in English, rain or shine, and is wheelchair accessible.

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15.Milan Skyscrapers Guided Tour: Porta Nuova, Unicredit tower & Vertical Forest

★★★★★★★★★★5.0 · 4 reviews · from $265

Spend three hours with a private art historian guide exploring Milan’s modern districts. Walk from Eataly through Corso Como and Piazza Gae Aulenti to the Unicredit Tower and Isola’s Vertical Forest, then sample Italian regional foods at Eataly.

“Abbiamo fatto questo tour in un caldissimo pomeriggio di Luglio .”

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