Chicago

We’ve compiled the best of the best in Chicago - browse our top choices for the top things to see or do during your stay.

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  • 1. 875 N. Michigan Avenue (formerly the John Hancock Center) and 360 Chicago

    Near North Side

    Designed by Skidmore, Owings & Merrill, this multipurpose skyscraper is distinguished by its tapering shape and enormous X braces, which help stabilize its 100 stories....Read More

  • 2. Auditorium Theatre

    South Loop

    Hunkered down across from Grant Park, this 110,000-ton granite-and-limestone behemoth was an instant star when it debuted in 1899, and it didn't hurt the careers...Read More

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  • 3. Chicago Cultural Center

    Chicago Loop

    Built in 1897 as the city's original public library, this huge building houses the Chicago Office of Tourism Visitor Information Center, as well as a...Read More

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  • 4. The Rookery

    Chicago Loop

    This 11-story structure, with its eclectically ornamented facade, got its name from the pigeons and politicians who roosted at the temporary city hall constructed on...Read More

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  • 5. Tribune Tower

    Near North Side

    Big changes have arrived at this iconic tower, which opened in 1925 to house the Chicago Tribune. Sold by the Tribune Company to CIM Group...Read More

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  • 6. Willis Tower

    Chicago Loop

    Designed by Skidmore, Owings & Merrill in 1974, the former Sears Tower was the world's tallest building until 1996. The 110-story, 1,730-foot-tall structure may have...Read More

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  • 7. Wrigley Building

    Near North Side

    The gleaming white landmark—designed by Graham, Anderson, Probst & White and the former headquarters of the chewing-gum company—was instrumental in transforming Michigan Avenue from an...Read More

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  • 8. 150 North Michigan Avenue

    Chicago Loop

    Some wags have pointed out that this building, with its diamond-shape top, looks like a giant pencil sharpener. Built in 1984 as the Smurfit-Stone Building...Read More

  • 9. 190 South LaSalle Street

    Chicago Loop

    This 40-story postmodern office building, resembling a supersized château, was designed by John Burgee and Philip Johnson in the mid-1980s. The grand, gold-leaf vaulted lobby...Read More

  • 10. 224 South Michigan Avenue

    Chicago Loop

    This structure, designed in 1904 by Daniel Burnham, who later moved his office here, was once known as the Railway Exchange Building and the Santa...Read More

  • 11. 311 South Wacker Drive

    Chicago Loop

    The first of three towers intended for the site, this pale pink edifice is the work of Kohn Pedersen Fox, who also designed 333 West...Read More

  • 12. 333 West Wacker Drive

    Chicago Loop

    This green-glazed beauty doesn't follow the rules. Its riverside facade echoes the curve of the Chicago River just in front of it, while the other...Read More

  • 13. 71 S. Wacker

    Chicago Loop

    At 48 stories, this modern high-rise is no giant, but it more than makes its mark on South Wacker Drive with a bold elliptical shape,...Read More

  • 14. 860–880 N. Lake Shore Drive

    Near North Side

    These 26-story twin apartment towers overlooking Lake Michigan were an early and eloquent realization of Mies van der Rohe's "less is more" credo, expressed in...Read More

  • 15. Aon Center

    Chicago Loop

    With the open space of Millennium Park at its doorstep, the Aon Center really stands out. Originally built as the Standard Oil Building, the 83-story...Read More

  • 16. Aqua

    Chicago Loop

    With its undulating concrete balconies suggesting rippling liquid, Aqua’s addition to the skyline in 2009 made Jeanne Gang a household name in architectural circles; the...Read More

  • 17. Bloomingdale's (Medinah Temple)

    River North

    Built in 1912 for the Shriners, the former Medinah Temple is a Middle Eastern fantasy, with horseshoe-shape arches, stained-glass windows, and intricate geometric patterns around...Read More

  • 18. Carbide and Carbon Building

    Chicago Loop

    Designed in 1929 by Daniel and Hubert Burnham, sons of the renowned architect Daniel Burnham, this is arguably the jazziest skyscraper in town. A deep-green...Read More

  • 19. Chase Tower

    Chicago Loop

    This building's graceful swoop—a novelty when it went up—continues to offer an eye-pleasing respite from all the surrounding right angles; and its spacious, sunken bi-level...Read More

  • 20. Chicago Board of Trade

    Chicago Loop

    Home of the thriving financial district, relatively narrow LaSalle Street earned the moniker "The Canyon" (and it feels like one) because of the large buildings...Read More

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