The 4 Best Skyscraper Tours in Chicago

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

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

See Chicago by car, riverboat, and Skydeck in about four hours. Your guide, such as Tony, Robert, Joe, or Danny, handles downtown pickup, tickets, city driving, and photo stops. Expect a fast-moving visit for up to seven people, with the Chicago River architecture cruise as the main event.

“Our tour guide Danny was prompt, knowledgeable and fun to be around. We had an exclusive tour since the other couple rescheduled.”

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2.Chicago Walking Tour: Art Deco Skyscrapers Loop

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

Walk through Chicago’s Loop with a Chicago Architecture Center certified guide, spotting Art Deco details at 30 N LaSalle, the Rookery, 135 S LaSalle, 1 N LaSalle, and the Board of Trade. Expect a small group of up to 10 people, selected interior visits, and gallery admission at the Chicago Architecture Center.

“This tour is a must on a visit to Chicago... so much of the city's earlier 20th century history is captured in this tour of the moderne art deco architecture. One does not tend to appreciate these gems hidden among the neo-classic buildings and glass high rises, but once seen, a lasting impression that will keep us looking in the future. Leaves one with the question if in 80 years people will be making glass and steel tours. Somehow, one doesn't get the feeling of enduring beauty as one does with Art Deco.... The detail work on the interiors of these amazing buildings is beautiful, and quite lacking in anything…”

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3.Chicago Walking Tour: Art Deco Skyscrapers Riverfront

★★★★★★★★★★5.0 · 53 reviews · from $35

Walk from the Chicago Architecture Center to THE MART, stopping at five Art Deco landmarks along the riverfront and in the Loop. You may enter grand lobbies at the Carbide and Carbon Building, former Chicago Motor Club, Trustees System Service Building, and Merchandise Mart, though access can change. Guides such as Mitch, Ron Roman, and Marcia add history and sharp detail.

“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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4.Art Deco Skyscrapers Walking Tour

★★★★★★★★★★4.8 · 28 reviews · 1h 30m

Meet your Chicago Architecture Center docent at 30 N LaSalle Street for a small-group walk through five Art Deco skyscrapers near the Chicago River. See geometric interiors, learn about 1920s design, and finish at the Merchandise Mart. Your ticket also includes admission to the Center’s exhibits.

“A lovely man, funny and knowledgeable about his subject!”

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