A Business Traveler's Guide to Chicago

401 N. Wabash Avenue, Chicago, IL 60610 (map)

A stay at one of the city's classiest hotels can't be bad for business. Give your clients the royal Trump treatment with a breakfast meeting at elegant Sixteen, the 16th-floor restaurant with a seasonal menu, elegant ambiance and floor-to-ceiling views of the Chicago River and the Wrigley Clock Tower. Concierge-arranged airport transportation (in a Lincoln Town car, Mercedes or limousine) and complimentary storage assures hassle-free arrival and departure.

240 E Ontario St, Chicago, IL 60611 (map)

Turn to this Streeterville offshoot of the city’s oldest sushi bar when you’ve got international clientele and must-impress guests. The spacious and airy dining room with Japanese shoji screens is just as impressive as the extravagant sushi boats and deluxe assortment of eye-catching sashimi. Three private rooms--two with tatami service and one with projection screen capabilities--accommodate large group meetings or presentations.

626 N State St, Chicago, IL 60610 (map)

Business types who appreciate the authentic Italian experience will enjoy the small plates at this casually sophisticated downtown restaurant. Square wooden tables are as rustic as the food, which includes staples like veal Milanese and mushroom risotto, plus cheeses and cold plates like Sicilian eggplant salad. Serving food daily until 1am, this lively dining spot is your room-service alternative if your flight arrives late.

1028 N Rush St, Chicago, IL 60611 (map)

This venerable Gold Coast steakhouse delivers iconic Chicago dining with elegant art deco decor. Dig into a timeless and business-appropriate menu of big porterhouses, T-bones, Florida stone crab claws and shareable sides like mashed potatoes. Six private rooms, each holding between 12 and 200 people, offer spacious dining for large groups.

1 W Washington St, Chicago, IL 60602 (map)

That early morning breakfast meeting dilemma is solved at this intimate restaurant tucked into the mezzanine level of the Burnham Hotel. Solid breakfast fare ranges from traditional eggs Benedict to banana pecan waffles and mascarpone-stuffed brioche French toast. The eclectic but serious decor--red curtains, black furniture and floor-to-ceiling windows--is a sumptuous backdrop for an efficient yet enjoyable morning meeting. A private room can accommodate up to 80 for a meeting.

505 North Michigan Ave, Chicago, IL 60611 (map)

The elegant, business-friendly environs at this Mag Mile wine bar--dark wood communal tables with buttery yellow chairs--are perfect for after-dinner social gatherings. What's not to like with 300-plus types of global wine served by the bottle, glass or flight, which can be paired with the 35 international varieties of cheese and locally crafted artisanal chocolates?

16 W Ontario St, Chicago, IL 60610 (map)

Colleagues find a break from the grind with nightly live music and spirited sing-alongs. A crowd of locals and tourists sips on aged Scotch, cognac, and martinis, and the cigars for sale are just as old school as the piano singers belting out "Sweet Caroline." Fans can stay as late as 4am, Sunday through Friday, and until 5am on Saturday.