A Mighty Plan

A new breeze blows through Chicago.

A new breeze blows through Chicago.

These days, dismissing Chicago as simply one of the fly-over states is passé. Nor is it any longer, as poet Carl Sandburg phrased it, “hogbutcher to the world.” In fact, the Windy City is now being touted for its burgeoning restaurant scene, fashion-forward boutiques and standout architecture.

Of course, it didn’t hurt when Vince Vaughn squired his then-love Jennifer Aniston around town (even throwing out a pitch at a Cubs game while Aniston watched in the stands), and that stars like Brad and Angelina have been snapped by paparazzi cruising Lake Michigan with their brood in tow. And, yes, there’s Oprah. Regardless of the celebrity appeal, Chicago is proving that it is a city, indeed, to again quote Sandberg, of “big shoulders.”

The city rebuilt itself once after the Great Fire in 1871, and it’s undergoing the same kind of rebirth today. In 2004, construction was completed on Millennium Park, a $500 million public space that features an impressive collection of postmodern architecture, including the Frank Gehry–designed Jay Pritzker Pavilion. A year later, the defunct rock concert Lollapalooza began again—moving to its now-permanent home in downtown’s Grant Park. Then last year, the Chicago History Museum underwent a major overhaul—renovating three-quarters of the building and adding a restaurant, overseen by Wolfgang Puck. And in the spring, the Chicago Loop Alliance hosted Looptopia, a one-day festival of live music, dance and theater performances. (Organizers are planning for another event in 2008.)

While the rest of the world begins to rediscover Chicago, there are some for whom the city has always been “my kind of town.”

“I just love jogging along Lake Michigan, where my parents live,” says New York socialite Jamee Gregory (who gave up Chicago for Manhattan). “It goes for miles in both directions and is a great way to start the day.”

But take it from the native: Chicago winters are cold. “You need sunglasses and a wrap,” advises Gregory as a way to battle the wind.

And, in a fashionable bonus: “It’s the perfect city for fur.”

As one resident put it, “If you are bored in Chicago for 15 minutes, you aren’t really trying.” The mercury takes a nosedive during the winter months, so Chicago has plenty of indoor attractions, namely the theater. The city boasts an impressive roster of storefront theater—where the likes of David Schwimmer, who founded Lookingglass Theatre Company, and Jeremy Piven, whose mother, Joyce, owns the Piven Theatre workshop in nearby Evanston—occasionally perform. Chicago is also home to the Steppenwolf Theater Company, which counts members like Joan Allen, John Malkovich and John Mahoney, and Second City, the famed improv club that launched the careers of comedians such as Stephen Colbert, Tina Fey, Amy Sedaris and Mike Meyers. And let’s not forget this is the city that gave us the Cusacks.

There’s also a great art scene, with no fewer than four major museums. The Chicago Art Institute is best known for its collection of French Impressionist and Postimpressionist paintings and also houses Grant Wood’s iconic American Gothic. A Jasper Johns exhibit will run until the beginning of next year.

The newly opened Chicago History Museum houses an assortment of city artifacts, including Abraham Lincoln’s deathbed, and in September, it will exhibit 50 couture pieces from its costume collection with labels such as Lanvin, Comme des Garçons, Chanel and Versace in the mix. The Museum of Contemporary Art is running an exhibit of rock ’n’ roll photography and art, titled “Sympathy for the Devil,” through January 6, and the Field Museum is best for those who get their kicks out of dinosaur bones. But Chicago art isn’t just about museums—the city also boasts a slew of galleries. Until December 29, Printworks Gallery will feature “Elegy for Isabella Blow,” a series of photographs and prints of the late British fashion editor, by artist and writer Audrey Niffengger, author of the best-selling The Time Traveler’s Wife.

The architectural boat tour on the Chicago River is a must, cruising by buildings constructed by Frank Lloyd Wright, Frank Gehry and Rem Koolhaas.

Once you’ve had your fill of culture, there’s always ice-skating at the rink in Millennium Park.
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