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. 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

  • 2. 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

  • 3. 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

  • 4. Cadillac Palace Theatre

    Loop | Arts/Performance Venue

    Opened in 1926 as a vaudeville venue, the theater was designed to evoke the Palace of Versailles. As time went on, its popularity waned. During...Read More

  • 5. Chase Tower

    Loop | Building/Architectural Site

    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...Read More

  • 6. Chicago Antique Market

    West Loop | Market/Bazaar

    This famed indoor-outdoor flea market, held on the third Saturday and Sunday of the month from late March through mid-December, is Chicago's...Read More

  • 7. Chicago Board of Trade

    Loop | Financial Institution

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

  • 8. Dearborn Station

    South Loop | Building/Architectural Site

    Part of Printers Row, this is Chicago's oldest-standing passenger train station, designed in the Romanesque Revival style in 1885 by New York...Read More

  • 9. Division Street

    Ukrainian Village/Wicker Park | Neighborhood/Street

    At the southern border of Wicker Park, Division Street has become a shopping and dining destination in its own right. Bars, boutiques, and trendy...Read More

  • 10. Franklin Building

    South Loop | Building/Architectural Site

    Built in 1888 as the home of the Franklin Company, one of the largest printers at the time, this building has intricate decoration. The tile...Read More

  • 11. Fulton Market

    West Loop | Neighborhood/Street

    This stylish neighborhood is filled with chic restaurants, trendsetting galleries, shops, and showrooms for cutting-edge design and green living...Read More

  • 12. Greektown

    West Loop | Neighborhood/Street

    This small strip may as well be half a world away from the rest of the West Loop. Greek restaurants are the main draw here. Continue west on...Read More

  • 13. Inland Steel Building

    Loop | Building/Architectural Site

    A runt compared to today's tall buildings, this sparkling 19-story high-rise from Skidmore, Owings & Merrill was a trailblazer when it was...Read More

  • 14. Macy's

    Loop | Store/Shop/Mall

    This neoclassical building, designed by Daniel Burnham, opened in 1907 as one of the world's earliest department stores, Marshall Field's. Macy...Read More

  • 15. NBC Tower

    Near North | Building/Architectural Site

    This 1989 limestone-and-granite edifice by Skidmore, Owings & Merrill looks back to the art deco days without becoming a victim of fashion...Read More

  • 16. Prudential Plaza

    Loop | Building/Architectural Site

    There are two architecturally notable buildings at the plaza. Directly west of the Aon Center and across from Millennium Park is One Prudential...Read More

  • 17. Reliance Building

    Loop | Hotel–Sight

    The clearly expressed, gleaming verticality that characterizes the modern skyscraper was first and most eloquently articulated in this trailblazing...Read More

  • 18. Sullivan Center

    Loop | Store/Shop/Mall

    From 1899 to 2007 this was the flagship location for the department store Carson, Pirie, Scott & Co. The work of one of Chicago's most renowned...Read More

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