Rising up from the southwestern edge of oceanic Lake Michigan, Illinois’ largest city (and the nation’s third-largest metropolis) has endured devastating fires, Al Capone’s corruption and beleaguered baseball teams. Yet its hearty Midwestern character not only endures but flourishes, with dazzling architecture, gritty blues, innovative live theater and comedy, world-class restaurants and a welcoming heartland disposition.
Most visitors stay in or near the downtown “Loop," the central business district circumscribed by the elevated metro tracks, and there are ample attractions here, from the nation’s tallest skyscraper, Willis Tower (formerly known as the Sears Tower); to the Beaux-Arts Chicago Cultural Center, boasting elaborate mosaics and the world's largest Tiffany glass dome; to the resplendent civic green spaces of Grant and Millennium Park. The justly renowned Art Institute of Chicago can constitute an afternoon alone. And in warm weather, there is no better introduction to the city than a fascinating architectural boat tour along the river (the Chicago Architecture Foundation has the best).
But to really get to know Chicago, venture out into the neighborhoods, exploring the North Side’s theaters, bars and clubs (and its vintage baseball stadium, Wrigley Field), or the bohemian havens of the West Side, where, in Wicker Park, an independent arts scene thrives and Polish and Ukrainian businesses and cultural attractions offer a taste of the city’s Slavic roots. A remarkable string of parks, beaches and marinas borders the entire eastern side of the city and Lake Michigan.
A Vintage Boutique
The historic Tree Studios building houses one of my favorite shops in Chicago, P.O.S.H. (613 North State Street. Tel.  280-1602). This bright boutique specializes in vintage serving ware from upscale hotels, cruise ships and restaurants. Sources include European flea markets, London auction houses and china warehouses. My most cherished find remains some mint-condition American Airlines first-class china.
It is wonderfully romantic (and great fun for small groups) to rent a boat for a couple of hours from the Chicago Electric Boat Company. Cruise the Chicago River, lined with some of the world’s most architecturally significant skyscrapers, and finish near Navy Pier, which has fireworks displays on Wednesdays and Saturdays in season. Bring Champagne.
The Home of Frank Lloyd Wright
Frank Lloyd Wright lived in the near-west suburb of Oak Park from 1889 to 1909, and his home and studio welcome visitors. He used his house to experiment with forms that later appeared in larger projects, and the tour is well worth the inconvenience of a trip out to Oak Park.
Magic and Drinks
Recently, a magic-themed bar opened on the city’s north side in a former laundromat. To enter the Chicago Magic Lounge (5050 North Clark Street, Tel.  366-4500), press the green button on the washing machine at the left of the vestibule. Inside is a surprisingly stylish bar with a space for small-scale magic at its center. There is no cover charge, but tickets are required to enter the main theater. The best restaurant nearby is Bar Roma (5101 North Clark Street, Tel.  942-7572).