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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  • Auditorium Theatre

    1. Auditorium Theatre

    South Loop | Arts/Performance Venue

    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...Read More

    Auditorium Theatre
  • 2. Chicago Cultural Center

    Loop | Building/Architectural Site

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

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  • John Hancock Center and 360° Chicago

    3. John Hancock Center and 360° Chicago

    Near North | Building/Architectural Site

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

    John Hancock Center and 360° Chicago
  • 4. National Veterans Art Museum

    Far Northwest Side | Museum/Gallery

    Located in Portage Park, this museum is dedicated to collecting, preserving, and exhibiting art inspired by combat and created by veterans....Read More

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  • The Rookery

    5. The Rookery

    Loop | Building/Architectural Site

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

    The Rookery
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  • Tribune Tower

    6. Tribune Tower

    Near North | Building/Architectural Site

    To create a home for his newspaper, Chicago Tribune publisher Colonel Robert McCormick held a design competition in which entrants were judged...Read More

    Tribune Tower
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  • Willis Tower

    7. Willis Tower

    Loop | Building/Architectural Site

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

    Willis Tower
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  • 8. Wrigley Building

    Near North | Building/Architectural Site

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

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  • 9. 150 North Michigan Avenue

    Loop | Building/Architectural Site

    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...Read More

  • 10. 190 South LaSalle Street

    Loop | Building/Architectural Site

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

  • 11. 224 South Michigan Avenue

    Loop | Information Center

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

  • 12. 311 South Wacker Drive

    Loop | Building/Architectural Site

    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 Wacker...Read More

  • 13. 333 West Wacker Drive

    Loop | Building/Architectural Site

    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...Read More

  • 14. 860–880 N. Lake Shore Drive

    Near North | Building/Architectural Site

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

  • 15. Aon Center

    Loop | Building/Architectural Site

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

  • 16. Bank of America Theatre

    Loop | Building/Architectural Site

    On Monroe, near State Street, the ornate Bank of America Theatre (formerly the LaSalle Bank Theatre and before that the Shubert Theatre) stages...Read More

  • 17. Bloomingdale's (Medinah Temple)

    River North | Building/Architectural Site

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

  • 18. Cantigny Park


    The 500-acre estate of former Chicago Tribune editor and publisher Robert McCormick (1880–1955) has multiple attractions. For starters, there...Read More

  • 19. Carbide and Carbon Building (Hard Rock Hotel)

    Loop | Building/Architectural Site

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

  • 20. Charnley-Persky House Museum

    Gold Coast | Building/Architectural Site

    Designed by Louis Sullivan and his protégé Frank Lloyd Wright, this almost austere residence is one of the few extant buildings that displays...Read More

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