Skydeck Chicago at Willis (Sears) Tower
Take the ear-popping ride to the 103rd-floor observatory, where on a clear day you can see as far as Michigan, Wisconsin, and Indiana. Fearless folks can step out onto the Ledge, twin glass boxes extending 4.3 feet from the Skydeck and suspended a dizzying 1,353 feet above the city.
John Hancock Center
The third-tallest building in Chicago has the most impressive panoramic views of the lake and surrounding skyline—it's high enough to see the tops of neighboring buildings, but not so remote that you feel as if you're looking out from a plane. The observatory recently changed its name to 360 Chicago, and added a new attraction on the 94th floor called Tilt, in which brave visitors lean against full-length windows (while holding onto metal support bars). If you'd like to skip the observatory, head to the bar that adjoins the Signature Room restaurant on the 95th floor—you'll spend your money on an exorbitantly priced cocktail instead of the observatory entrance fee and enjoy a great view.
The Magnificent Mile
Exclusive shops, department stores, and boutiques line the northern half of swanky Michigan Avenue. Even better, the concentration of prestigious stores in vertical malls means you can get a lot of shopping done in winter without venturing into the bluster outside.
Yes, it's a little schlocky, but Navy Pier is fun, especially for families. Everyone can fan out to shop in the mall, play 18-hole minigolf in Pier Park in summer, see a movie at the IMAX Theatre, or explore the Chicago Children's Museum. Plus, there's a stained-glass museum, a fun-house maze with scenes of Chicago landmarks, and an old-fashioned swing ride.
Art Institute of Chicago
This Chicago cultural gem has the country's best collection of impressionist and postimpressionist art, as well as the Renzo Piano–designed modern wing. It's also a great place to see all those paintings you've seen only on postcards, like American Gothic and Nighthawks.
Say hello to Sue, the Field's beloved gigantic T. rex, before immersing yourself in this extraordinary museum's collection of anthropological and paleontological artifacts and animal dioramas. The dinosaurs are the thing here, but surprising collections of Tibetan Buddhist altars, mummies, and re-creations of famous gems may entice you to linger for hours.
We find the experience of watching entire universities—not just schools—of fantastically colored fish, as well as dolphins and whales, completely mesmerizing. Don't miss the Wild Reef exhibit, where stingrays slide quietly under the Plexiglas at your feet.
Make a beeline for Frank Gehry's Jay Pritzker Pavilion, where an incredible sound system allows audiences to enjoy concert-hall sound in the great outdoors. The Bean, formally known as Cloud Gate, is a luminous polished-steel sculpture that plays tricks with the reflection of Chicago's skyline. In warmer months children of all ages can't resist a splash in the Crown Fountain, twin 50-foot towers that project close-up video images of Chicagoans "spitting" jets of water.
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