The sign I found taped to my office door one morning made me feel like a Chicago native. "Concierge," it read, a gentle tease from colleagues who had endured my monologues about the Windy City's food, music, sports teams, and history.
As a lifelong Easterner who arrived here in 1997, I'm fascinated with a place often described as the quintessential American city. Its downtown may cater to convention-goers, but Chicago is a city that rewards the curious. The Midwest's undisputed capital, it combines big-city energy with prairie simplicity.
Normally, I advise folks to skip the obvious tourist spots. But not this one: Start your tour of the Windy City by heading for 875 Michigan Ave. (table). There, on the glitzy shopping strip known as the Magnificent Mile, sits the John Hancock Tower, the city's best modern skyscraper. Zip up to the 96th floor and step into the elegant bar featuring the same spectacular views you'd get at the taller Sears Tower or the Hancock observation deck two floors below. Here, though, there are no lines or fees. Order a Goose Island Honkers Ale, a local microbrew, and marvel at Lake Michigan's varying shades of blue.
With this grand scale of Chicago in mind, you'll be ready to enjoy the city's renowned architecture. While the towering Board of Trade (141 W. Jackson) and the starkly illuminated Wrigley Building (410 N. Michigan Ave.) may stand out, the Rookery Building (209 S. LaSalle) is the favorite of many Chicagoans. Why? A magnificent lobby, naturally lit by a glass ceiling, designed in 1886 by Burnham & Root, redesigned by Frank Lloyd Wright, and restored in 1992.
If you're hungry, a short ride by cab or on the high-speed El will vault you beyond the theme restaurants to eateries popular among locals. Try the artsy Bucktown enclave, four miles northwest of the Loop. Club Lucky, a converted Veterans of Foreign Wars hall, boasts tasty Italian bistro fare that draws a nice mix of families and funky twentysomethings. Dinner for two runs about $40.
For an authentic ethnic setting, go southwest from the Loop toward Pilsen, once filled with Eastern Europeans. Now it's home to some of the city's large Mexican population. The Spanish-speaking neighborhood has a main artery, 18th Street, lined with brightly painted brick buildings and small shops. Stop at Decima Musa (1901 S. Loomis, 312 243-1556) for such dishes as milanesa (breaded steak) or huachinango (snapper). Dinner for two will cost about $50, but you can eat lunch for less than $10 each.
GRAND HOTELS. For evening entertainment, pick up a copy of The Chicago Reader, a free weekly that will lay out your options. Two good bets for blues: Rosa's on the North Side and the Checkerboard Lounge on the South Side. Both are far better than the downtown clubs catering to tourists.
There's only one place where your night should end: the Old Town Ale House, about two miles north of the Loop. It is a bar lover's bar, open daily until at least 4 a.m. A replica Maltese Falcon guards the counter, a jukebox thumps out Art Blakey and Bob Dylan, and actors from the next-door comic troupe Second City quaff their beers.
Wherever you spend the night, stop at the lobby of one of the city's grand old hotels, like the Drake (140 E. Walton St., 312 787-2200) on the Magnificent Mile or the Palmer House Hilton (17 E. Monroe St., 312 726-7500). If you're still seeking things to do, both have concierges who can help. But don't call me--I'll probably be out on the town, researching another spot and trying to keep my office reputation intact.