Checking In: Chicago

Checking In: Chicago

People come to Chicago in search of dreams and to start new lives and new businesses, says Cheryl Burton, a television news anchor at ABC 7 News, of a town founded by a free black entrepreneur, Jean-Baptiste Point DuSable, in the 1700s. Burton, a native of Chicago’s South Side, notes that some of the city’s present business luminaries are considered living legends: Michael Jordan, Oprah Winfrey, and John H. Johnson of Johnson Publishing Co.

That spirit of achievement is also reflected in Chicago’s larger business community. Fortune 500 firms based in the Windy City include Motorola Inc. and The Boeing Co. The city is also one of the nation’s largest convention and trade show destinations.

“Chicagoans are very warm and welcoming,” offers Burton of the city’s nearly 4 million residents. “We like to say Chicagoans are ambassadors for the United States.” Here, Burton offers a city tour.


  • Well-heeled visitors favor The Peninsula Chicago (108 E. Superior St.; 312-337-2888), says Burton. “World travelers like to come here because they’re familiar with the name. The service is incredible.”
  • Four Seasons Hotel Chicago (120 E. Delaware Pl.; 312-280-8800) stands atop Chicago’s “Magnificent Mile.” “There’s nothing they can’t provide for you,” says Burton, who loves afternoon high tea while overlooking Michigan Avenue.
  • The chic favor the W Chicago—City Center (172 W. Adams St.; 312-332-1200). “It’s eclectic, very hip, and the energy is very upbeat.” Plus, it’s within walking distance of Chicago’s burgeoning theater scene.


  • Japonais (600 W. Chicago Ave.; 312-822-9600), housed in a former catalog warehouse on the Chicago River, is an exotic sushi spot “where the rich and famous hang out. Dining on the river on a hot summer night—it doesn’t get much better than that.”
  • Major deals go down at the carnivore-friendly Gibsons Steakhouse (1028 N. Rush St.; 312-266-8999), a Gold Coast gem. Burton says you’ll find everyone “from heads of state [to] some of the highest-paid athletes.”
  • For the best biscuits north of Nashville, Burton swears by Sweet Maple Café (1339 W. Taylor St.; 312-243-8908). This cozy, black-owned, 14-table eatery, not far from downtown, draws down-home food lovers of all races. As for the salmon cakes, says Burton, “They make ’em like your mama used to make ’em.”


  • The Shark Bar (212 N. Canal St.; 312-627-0800) draws upscale African Americans to its riverfront location. This spot features jazz on Thursday nights.
  • Green Dolphin Street (2200 N. Ashland Ave.; 773-395-0066) draws a stylishly diverse clientele seeking great live music—including jazz—in a swanky atmosphere.


  • Burton loves The Spa and Fitness Club at the Four Seasons Hotel Chicago (120 E. Delaware Pl.; 312-649-2340). “Even the cucumber water tastes really good.” Aside from workout facilities and an assortment of spa treatments, it provides a 59-foot swimming pool to help business travelers unwind.

“Taxi service in Chicago is prompt, available, and you can always find [one] 24 hours a day.”