17 Jan Time Out: Chicago

If you’ve got business in what may be this country’s most multi-monikered city—Chi-town, also know as the City of Broad Shoulders, the Windy City, Second City, and That Toddling Town—be sure to make time to play as well as work: Chicago’s beguiling leisure choices outnumber its nicknames by a thousand to one.

The city’s humming downtown, centered around the commercial riverfront nexus known as the Loop, is packed with attractions. Landmark buildings shoot upwards—the 40-mile view from Sears Tower‘s 103rd-floor Skydeck is a must-see—as do monumental outdoor sculptures by luminary artists. In a few blocks’ span you can clamber on a Picasso, recline against a Calder, or stroll beneath the arch of the mammoth, silvery bean—otherwise known as Cloud Gate—that Indian-born British sculptor Anish Kapoor designed for Millenium Park, a glorious recent addition to the city’s band of recreation areas fronting Lake Michigan. Downtown is also dotted with major cultural institutions, from the 1929 Art Nouveau-style Civic Opera House to the stately Art Institute of Chicago, and a limitless supply of luxury shops; Ferragamo, Zegna, Armani, Vuitton, and Chanel (among others) rub well-clothed elbows along North Michigan Avenue’s “Magnificent Mile.”

Beyond downtown, a scattering of proud ethnic enclaves offer idiosyncratic temptations. Just west of the Loop, where Greek Town’s boutiques and restaurants cluster along S. Halsted Street, you can stock up on frankincense and myrrh (not commonly available at your nearest mall!) at the Athenian Candle Co., then fill up on Mediterranean delicacies at Greek Islands. Food is also an attraction in Little Italy (RoSal’s, a true family business where the dining room walls are crammed with framed photos of the owners’ children and the owners as children, is a favorite) and in Chinatown (head to Happy Chef Dim Sum House for authentic Cantonese treats).

Further south, you can take yourself out to the ball game at U.S. Cellular Field, home of the 2005 World Series-winning White Sox, or take in exhibits exploring the achievements of African Americans at the DuSable Museum of African American History. To the north, name-brand chefs vie for your palate’s attention: Heat up with mouth-watering Mexican creations at Rick Bayless’ Topolobampo, or savor elegant, seasonal American cuisine at Charlie Trotter’s. Once you’re sated, check out Carter’s Way, a jazz-filled play “of love, lust, and an artist’s integrity” playing through May at Steppenwolf Theatre; or head further north to get your music served straight up at prohibition-era Green Mill Jazz Club. Wherever you go, Chicago will live up to its newest nickname: the City (that) Has It Comin’ and Goin’ On.

The Play by Play

All area codes are 312 unless otherwise noted.

Eats

Charlie Trotter’s, 816 W. Armitage, (773) 248-6228

Greek Islands Restaurant, 200 S. Halsted St., 782-9855

Happy Chef Dim Sum House, 2164 S. Archer Ave., 808-3689

RoSal’s Italian Cucina, 1154 W. Taylor St., 243-2357

Topolobampo, 445 N. Clark Street, 661-1434