36 Best Sights in The Loop, Chicago

There are two architecturally notable buildings at the plaza. Directly west of the Aon Center and across from Millennium Park is One Prudential Plaza. Designed by Alfonso Iannelli and completed in 1955, this limestone-and-ridged-aluminum structure was once the city's tallest building (barring the statue of Ceres atop the Board of Trade). At the time, it had the world's fastest elevators and an observation deck that became passé once some of the city's other behemoths were completed. Attached to One Prudential is its sibling Two Prudential Plaza, nicknamed "Two Pru," a towering glass-and-granite giant with an address of 180 North Stetson Avenue. Along with their neighbors they form a block-long business-oriented minicity. Two Prudential is the tallest reinforced concrete building in the city, and its blue detailing and beveled roof are instantly recognizable from afar.

The clearly expressed, gleaming verticality that characterizes the modern skyscraper was first and most eloquently articulated in this trailblazing steel-frame tower, built by Burnham, Root, and Charles Atwood. Completed in 1895 and now home to the stylish Staypineapple Hotel, the building was a crumbling eyesore until the late 1990s, when the city initiated a major restoration. In the early and mid-1900s, it was a mixed-use office building. Al Capone's dentist reportedly worked out of what's now Room 809. Don't be misled when you go looking for this masterpiece—a block away, at State and Randolph streets, a dormitory for the School of the Art Institute of Chicago shamelessly mimics it. Once you've found the real thing, admire the mosaic floor and ironwork in the reconstructed elevator lobby. The building boasts early examples of the Chicago Window, which define the entire facade by adding a shimmer and glimmer to the surrounding white terra-cotta.

Named for late mayor Richard J. Daley, this boldly plain high-rise is the headquarters of the Cook County court system, but it's best known as the site of a sculpture by Picasso. Simply dubbed the Picasso, this monumental piece provoked an outcry when it was installed in 1967; baffled Chicagoans tried to determine whether it represented a woman or an Afghan hound. In the end, they gave up guessing and simply embraced it as a unique symbol of the city. The building itself was constructed in 1965 of Cor-Ten steel, which weathers naturally to an attractive bronze. In summer, its plaza is the site of concerts, political rallies, and a Thursday farmers' market. In December, Christkindlmarket (a traditional German market selling food and gifts) takes over the area.

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 architects, it combines Louis H. Sullivan's visionary expression of modern design with intricate cast-iron ornamentation. The eye-catching rotunda and the 11 stories above it are actually an addition Sullivan made to his original building. In later years D.H. Burnham & Co. and Holabird & Root extended Sullivan's smooth, horizontal scheme farther down State Street. The ground floor now houses a Target, with office tenants occupying the floors above.

Now home to the acclaimed Chicago Symphony Orchestra (CSO), this complex includes Orchestra Hall, built in 1904 under the supervision of Daniel Burnham. The Georgian building has a symmetrical facade of pink brick with limestone quoins, lintels, and other decorative elements. An interior renovation, completed in 1997, added a seating area that is behind and above the stage, allowing patrons a unique vantage point.

Running along both sides of Wabash Avenue from Ida B. Wells Drive south to 16th Street, this mile-long stretch is an outdoor gallery of murals and street art. There are nearly 40 permanent installations and an evolving set of temporary exhibitions. Chicago artists including Shepard Fairey, Hebru Brantley, and Sam Kirk have had work shown here.