Caroline is an 18-year-old woman from a small town who travels to Chicago to seek opportunity and material success. Equipped with only a high school education and no work experience, she initially faces the harsh reality of urban poverty working in a shoe factory. Her intense fascination with fashion, elegance, and the theater drives her ambition to rise above her modest beginnings. She views the affluent lifestyles of the city as the ultimate measure of happiness and social standing.

Charles is a traveling salesman with a genial demeanor, flashy clothes, and a charming, easygoing confidence. He acts as Caroline's early guide to the city, introducing her to better living conditions, dining, and the theater. Though good-natured and financially generous, he views relationships superficially, treating social interactions as extensions of his sales tactics.

George is the shrewd and capable manager of a high-class saloon in Chicago. He is a respected figure in his community, enjoying the comfortable lifestyle of a successful middle-class businessman. Despite his outward success and a stable townhouse on the North Side, he feels deeply dissatisfied with his emotionally empty marriage and longs for genuine affection.

Bob is a young graduate student in electrical engineering who possesses a sharp intellect and a pragmatic perspective. Unlike the other men in Caroline's life, he is unimpressed by wealth and status. He advocates for the importance of serious art and intellectual pursuits over shallow materialism, challenging Caroline to view the world differently.

Mrs. Hurstwood is George's wife of nearly twenty years. She is a self-centered woman focused on the social mobility of her teenage children and the financial advantages of her husband's position. She demands control over the family's resources and protects her social standing with fierce determination.

Minnie is Caroline's older sister who lives a modest, financially strained life in a small Chicago house with her husband and baby. She represents the grim reality of working-class domesticity, prioritizing rent payments and practical survival over leisure or ambition.

Mrs. Vance is a wealthy and beautiful woman living in New York. As an accomplished pianist and thorough-going materialist, she enjoys the affluent lifestyle that Caroline dreams of, regularly critiquing the fashion of other women on Broadway.

Mrs. Hale is a neighbor of Caroline's during her time living in a flat provided by Drouet. She exposes Caroline to the extravagant mansions and manicured landscapes of Lincoln Park, fueling the young woman's desire for luxury.

Lola is a fellow actor in the theater who recognizes Caroline's talent and becomes a reliable companion. She represents the independent lifestyle available to working women in the theatrical world, encouraging Caroline to embrace her stage opportunities.