Here's an insiders' guide to enjoying it all, even if you've got only a short window between meetings. The newest attraction for Chicagoans — and your first stop — is "the Bean": a 66-ft.-long, 110-ton quicksilver blob in Millennium Park, the new $475 million addition to the city's famous museum row. The reflective stainless-steel sculpture (which its British creator, Anish Kapoor, calls Cloud Gate) distorts North Michigan Avenue like a fun-house mirror. Weather permitting, you can check out architect Frank Gehry's dynamic bandshell at the Jay Pritzker Pavilion. (If you need to check email, the north and south ends of the park carry wifi Internet signals.)
From there, the options widen. If culture is your thing, pop across the street from Millennium Park to the Art Institute of Chicago, where you can see some of the world's most famous paintings, including Grant Wood's American Gothic and Georges Seurat's Sunday Afternoon on the Island of La Grande Jatte. If it's shopping you crave, check out a classic downtown department store, Carson Pirie Scott or Marshall Field, where if nothing else, you can pick up a box of famous Frango mints.
And when it's time for a drink, well, Chicago knows how to tend bar. You could visit the historic Berghoff on West Adams Street and the Coq d'Or in the Drake Hotel, the first two bars to tap a legal keg after Prohibition ended. But if you have time to leave the business district, head up to West Randolph's up-and-coming restaurant row to see how Gen X yuppies indulge themselves. You will also find them at the spacey Ghost Bar upstairs from Nine, Michael Morton and Scott DeGraff's new restaurant. On the far end of West Randolph, visit the Tasting Room, a four-year-old wine shop and warehouse bar. From the second floor, you can take in the entire skyline (and a glass of any of 110 wines on tap).
Once you've downed a glass or three, zip down the street to one of West Randolph's hip eateries, such as the Blue Point Oyster bar (an upscale diner that claims the city's freshest oysters), Sushi Wabi (if you like artful fish and don't mind tight spaces) or March (a latter-day French Surrealist bistro). Want quick takeout with local color? Grab an Italian beef sandwich at Mr. Beef's on Orleans. The hard core order it "wet," with the roll soaked in gravy.
The city is also known for its clubs, of course, and options abound beyond the famous Second City for comedy and Kingston Mines or Green Dolphin Street for jazz. Natives flock to Rosa's Lounge, a blues haven northwest of downtown run by Tony Rosa and his mother. You may not end up dancing in the streets, as Matthew Broderick's character did, but a few hours of R. and R. in Chicago will certainly feel like a day off.