Maggie Daley Park

1136 ft. Built as the Standard Oil Building, the Aon Center is America's sixth tallest building from base to roof, after the Empire State Building in New York City, and fifteenth tallest in the world by architectural detail. It was built in 1972 by architect Edward Stone and initially was faced with marble, but the windy city began to blow the marble off the sides of the building. The entire building had to be refaced with granite — a costly job at one-half of the entire building costs! A walk around the base can be particularly gratifying to admire the uninterrupted views straight up the shear walls and the "musical sculptures.".

823 ft. The biggest American project ever to be headed by a woman, Jeanne Gang's skyscraper was named the world's best new building by Emporis when it opened in 2009 (four spots ahead of the Trump Tower across the river). Its most distinguishing feature is its series of undulating balconies, which extend as far as twelve feet from the building's walls, giving the building a surreal "rippling" effect. It uses an unforgettable curtain wall that compliments wavy balconies. Though impressive from any angle, it's best viewed relative to the water — either from a boat tour or the riverwalk over in the Near North.

Long before it opened, Millennium Park had become notorious for delays and cost-overruns, missing its titular date by a wide margin. However, when it was finally finished in 2004, the biggest shock of all came when it turned out to be quite nice. Aside from plenty of grass and open space, it has modern sculptures in steel and glass, including Chicago's newest must-photo for visitors, The Bean (properly known as Cloud Gate), and the Frank Gehry-designed Pritzker Pavilion for outdoor concerts. Kids will love getting wet in the Crown Fountain (mid-April to the end of summer) at Michigan and Monroe, in which the giant projected faces of Chicago residents spit water into a shallow reflecting pool where everyone is welcome to splash around. Look for tents offering guides to the park near the entrances at Randolph and/or Washington. From mid-November to early March there is an ice skating rink open to the public (weather permitting) on Michigan Avenue between Washington and Madison Streets. The McCormick Tribune Ice Rink opens at noon on weekdays and 10AM on Saturdays and Sundays with free admission (skate rental is $12, locker rental is $1).

Built in 1897 as Chicago's first public library, the building now houses the city's Visitor Information Center, galleries, and exhibit halls. Worth a visit to see the beautiful interior — the ceiling of Preston Bradley Hall includes a 38-foot Tiffany glass dome, and the north wing includes the impressive Grand Army of the Republic Rotunda. Of late, amid various city-approved art and music events, some surprisingly good theater has been performed here.

582 ft. Anyone who has seen Adventures in Babysitting should immediately recognize this 1984 building, as its slanted roof (lit up at night) played a very important role in the film's climax. It's a hard building to miss, as it is just across the street from Millennium Park.

A beautiful Art Deco tower covered in dark green terra cotta and adorned with a gold terra cotta leaf at the pinnacle. It is rumored that the architects (the sons of city planner Daniel Burnham) intended the building to resemble a bottle of champagne. It's in great condition today, and can be visited through one of the bars in the lobby of the hotel inside.