Chicago Feature

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. At the top, interactive exhibits feature notable Chicagoans. Kids love Knee-High Chicago, a 4-foot-high exhibit that has cutouts of Chicago sports, history, and cultural icons at a child's eye-level. 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. Security is very tight, so figure in a little extra time for your visit to the Skydeck.

John Hancock Center Observatory

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 like you're looking out from a plane. Skip the observatory and 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 entrance fee and enjoy the same view. Women can head to the 95th-floor ladies' room for the best view in the whole building.

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.

Navy Pier

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 Theater, 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. Meet up later at the Ferris wheel for a photo op or just settle on the pier with a drink and enjoy the view.

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 only seen on postcards, like American Gothic and Nighthawks.

Field Museum

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.

Shedd Aquarium

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.

Millennium Park

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.