After its glorious success in New York city, the City Winery has extended its purview and opened an outlet in Chicago. This winery is more than just a place to sample wines, it is an entertainment hub of the city. Food and wine tastings, concert series, special lunches, fund-raising brunches and much more is hosted here. So while you sip and enjoy every bit of the fine wine, renowned artists/bands will entertain you. For upcoming events and other information, check its website.