Best place to experience local culture: "Espanola Way. You have Latin cafes alongside galleries with Cuban and European art. On Sundays, they have a street fair with handmade crafts."
Best outdoor cafe: "News Café is a
classic. They get a great clientele, the food is good, and they have a great outdoor scene."
Best people watching: "I send people to Nikki Beach. It's steps away from the ocean and has a huge outdoor area with tents and couches. Nikki Beach attracts a great mix of beautiful people."
THE DRAKE HOTEL
Best way to kill an hour: "Chicago is one of the world's few cities with a lakefront. It's right across the street from our hotel, and I like to send people there."
Best restaurant on an expense account: "Charlie Trotter's is an outstanding experience. People travel from around the world to eat there."
Best lunch on the run: "Mike Ditka's, which is owned by former Bears coach Mike Ditka, has the city's best crab cakes and hamburgers."
Best place to close a deal: "The Saloon Steakhouse is very clubby and is quiet enough for talking. Plus they make great steaks."
Best place to buy a suit or dress: "Mark Shale has wonderful work attire for men and women. They'll open at any hour for us, so that comes in handy."
Best place to buy a gift for the spouse: "Ultimo sells beautiful, upscale women's clothing imported from Europe."
Best place to buy gifts for the kiddos: "The American Girl Place is famous for dolls and storybooks. For boys, there's the Peggy Notebaert Nature Museum, with all kinds of educational, hands-on exhibits for kids who like to experiment."