Chicago in 1900 is bursting with opportunity, and Kitty Coakley is determined to make the most of it. The youngest of seven children born to Irish immigrants, she has little interest in becoming simply a housewife. Inspired by her entrepreneurial Aunt Mabel, who runs a millinery boutique at Marshall Field's, Kitty aspires to become an independent, modern woman. After her music teacher dashes her hopes of becoming a professional singer, she refuses to give up her dreams of a career. But when she is courted by not one, but two young men, her resolve is tested. Irish-Catholic Brian is familiar and has the approval of her traditional, working-class family. But wealthy, Protestant Henry, who is a young architect in Daniel Burnham's office, provides an entrée for Kitty into another, more exciting world. Will she sacrifice her ambitions and choose a life with one of these men?