Businesswise and otherwise, the city and its suburbs are nothing if not diverse, home to Boeing and United Airlines, Kraft Foods and Sara Lee, McDonald’s and the MacArthur Foundation, as well as Playboy, Ebony, and Poetry magazines.
Convention business is going great guns, its showpiece the glittering—and ever-expanding—McCormick Place, just south of downtown. The $475 million Millennium Park is the latest must-see attraction, with its flamboyant brushed-steel Jay Pritzker Pavilion designed by Frank Gehry, who, incidentally, calls Chicago America’s most visually exciting metropolis. With architecture that includes iconic buildings by Frank Lloyd Wright, Louis Sullivan, Ludwig Mies van der Rohe, and other modern masters, gawking is rewarded richly here.
Where to Stay
The most expensive and luxurious bastions of work/play synergy are concentrated near the landmark 1869 Water Tower. Celebrities, Armani-clad record executives, and international jet-setters cocoon themselves in The Peninsula, with its Art Deco–Asian minimalist decor and stunning penthouse spa. The gray-granite modernism of the nearby Park Hyatt, flagship of the architecture-loving Pritzker family’s chain of hotels, draws a slightly tweedier crowd of senior investment bankers, law partners, and old money Gold Coast doyennes. The Gordon family, the Tootsie Roll heirs, liked the hotel so much they bought one of its apartments. The knife-shaped Sofitel Chicago Water Tower pays homage to Mies van der Rohe with Barcelona chairs in several rooms. The Four Seasons, styled like a European palace atop a mixed-use high-rise, is close to Lake Shore Drive’s jogging path and beaches. Serious swimmers (and aficionados of 1920s-era opulence) favor the Hotel InterContinental down the street, with its enormous movie-worthy pool. Those who prefer cushiness with a modern aesthetic head for the cool-vibe James hotel or the Amalfi, both a short hop west of Michigan Avenue in River North. Nearer to Millennium Park and the trendy West Loop dining scene, the elegantly refurbished Hotel Burnham is a short dash from City Hall, the Federal Reserve Bank, and the financial district.
Where to Eat
The buzziest kitchen talent at the moment is Grant Achatz, chef-owner of Alinea, where the 22-course tasting menu combines classical technique and science fair–worthy presentation (cinnamon smoke bongs, lavender vapors). Book well in advance. At River North hot spots Topolobampo and its more casual sibling Frontera Grill, celebrity chef Rick Bayless fashions Oaxacan ingredients into haute cuisine. Dinner gets busy, but guests can order appetizers at the bar while waiting for a table. The Union Stockyards closed back in the ’70s, but this is still one meaty town, and steak houses are everywhere. At night, Chicago media, sports, and advertising crowds take out-of-town clients to Harry Caray’s, where the widow of the Hall of Fame Cubs announcer often holds court in a century-old space decorated with baseball memorabilia. Across the street, Keefer’s is a contemporary spot with excellent steaks and salads—easy to get in and out of for lunch, and a cab can put you back on Michigan Avenue in five minutes. Even quicker at lunchtime is Keefer’s Kaffe, next door, with its robust chili and hand-carved meat sandwiches, giant plasma TV, and stock ticker board.
Where to See and Be Seen
Overachievers flock to Gibson’s, a Rush Street steak house that has served presidents Bill and George W. You may not be able to hear your companions’ conversation, but that’s not the point at the 300-seat Japonais, whose waterfall, riverfront patio, subterranean cocktail lounge, and excellent French-Asian cuisine draws Sex and the City types. For night owls, the Rockit Bar & Grill has a massive upstairs bar with pool tables and leather couches. The sleekly stylish congregate at Avec for drinks and small plates before dinner at chic Blackbird, next door. The Peninsula Hotel Bar, with its dark-red walls, is a glamorous after-work spot.
Where to Close a Deal
Treat your guests to short ribs with horseradish cream puffs at the new and excellent Custom House, at the north end of Printer’s Row, and they’ll know you know from food as well as from business. At the literal apex of the city’s fine dining scene, Everest, on the fortieth floor of the Chicago Stock Exchange building, showcases chef Jean Joho’s fusion of Alsatian method and Midwest terroir. The old-world feel, great food, and solemn ambience make it a place clients won’t forget. For groups, NoMi, in the Park Hyatt, offers one of the city’s most elegant private dining rooms. Capital Grille draws repeat customers Michael Jordan and Playboy CEO Christie Hefner with its red meat and no-nonsense atmosphere.
Chicagoans love to wax lyrical on the greatness of their city. Indulge them and they may listen patiently as you describe what’s so terrific about your hometown. If asked to declare a preference for the Cubs or the Sox, declare neutrality. Baseball passions run deep.
Got time to kill? Hit the O’Hare Hilton Athletic Club for a workout, a swim, or a sauna. It’s an easy walk through a pedestrian tunnel. Day rates are only $11. For a pre-flight massage, visit the Backrub Hub in Terminal 3. Midway Airport travelers awaiting their plane can tune into George’s Music Room, a small but well-stocked CD store.
The Three-Hour Tour
Start with a 90-minute, docent-led boat cruise offered by the Chicago Architecture Foundation; it leaves from the southeast corner of the Michigan Avenue Bridge at Wacker Drive and takes you past dozens of modern and historic skyscrapers lining the Chicago River. After the cruise, a ten-minute walk south from the Michigan Avenue Bridge brings you to Millennium Park, a showstopping nexus of gardens, people watching, and flashy contemporary art. The park kiosk is the place to try a Chicago hot dog with all the fixings (no ketchup, by tradition, but do ask for yellow mustard, sweet relish, onions, pickled chili peppers, and celery salt). Finally, cab up Michigan Avenue and take an elevator to the top of the John Hancock Building for big picture views.
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