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This splendid 1909 residence by Frank Lloyd Wright is easily spotted by its steel-beam roof, which overhangs the building by 20 ft (6 m) at each end. Take a tour through its lowceilinged interior, and past more than 170 art-glass windows and doors, to gain insight into the ongoing, extensive ten-year restoration program. The building was a private home until 1926, when it became a dormitory for the Chicago Theological Seminary. It was later bought by a development firm, who donated it to the University of Chicago in 1963, the same year it was designated a National Historic Landmark.

An architectural superlative, the tower offers breathtaking bird’s-eye views from its 103rd floor Skydeck, where you’ll find yourself standing on top of 76,000 tons of steel (see Sears Tower & its Views).

How ironic that this bustling arts and community center, which serves a largely African-American demographic, began in 1905 as an exclusive country club that barred minority members. Designed by the team who later worked on the elegant Drake Hotel (see The Drake), this grand Mediterranean-style structure was bought and lovingly restored by the Chicago Park District when the country club fizzled out in the 1970s. Extravagant landscaping and flower beds complete the pretty picture, making it a popular spot for weddings and festivals, as well as for all kinds of performances and classes. Its golf course, nature park, and the public beach behind it add to its many draws.

This “great street” got its nickname from the 1922 hit song Chicago . Although it didn’t always live up to this catchy moniker, it has won back many fans since its multi-million-dollar face-lift in 1996. It now sports replica Art Deco lampposts and subway entrances, and was listed on the National Register of Historic Places in 1998. This dynamic stretch has it all: shopping, history, education, architecture, theater, and dining. The atmosphere is especially merry during the run up to Christmas, when the Thanksgiving parade brings Santa to town, and department stores like Marshall Field’s fill their windows with elaborate and imaginative decorations.

This 11-story building, with its rusticated red granite base, was the country’s largest office building and a precursor to modern skyscrapers when it was completed in 1888 by Burnham and Root (see Top 10 Architects). Its stunning skylit lobby was redesigned in 1907 by Frank Lloyd Wright (see Frank Lloyd Wright’s Oak Park), who added a grand staircase and hanging light fixtures, both of which carry his signature circle-in-square motif. The building’s unusual name refers to the rooks that once roosted at the site.

Noted for its research and high educational standards, this remarkable private university has produced over 70 Nobel Prize winners.

Strolling around the University of Chicago campus, there’s more of visual interest than its buildings alone. Over the years, the university has acquired around 12 outdoor sculptures, including Wolf Vostell’s whimsical 1970 Concrete Traffic , a car embedded in concrete at the southwest end of the Midway Plaisance and the sobering Nuclear Energy , a bronze by Henry Moore that resembles a mushroom cloud. Set within a reflecting pool at 60th Street and University Avenue is Construction in Space in the Third and Fourth Dimension , a soaring abstract piece created in the 1950s by Constructivist Antoine Pevsner, which visually depicts the space-time continuum.

Frederick Law Olmsted and Calvert Vaux, the designers of New York’s Central Park, also created this 371-acre (150-ha) green space for Chicago residents in the early 1870s. It originally attracted mainly wealthy city dwellers who enjoyed parading around the scenic space. Today, it’s a beautiful and widely used park with recreational programs, the DuSable Museum of African-American History, and Lorado Taft’s striking 110-ft (34-m) long sculpture, Fountain of Time , which took him 14 years to build. It is unwise to venture into the park after dark.