At age 18, Caroline Meeber, or Sister Carrie as her family calls her, boards the train from her small-town home of Columbia City, Wisconsin to Chicago. Although she has no work experience and only a high school education, Carrie is undaunted; she is a “half-equipped little knight” (2) on a mission to succeed. Initially, she plans to stay with her sister, Minnie, and her family.

On the train, Carrie chats with a man sitting behind her. She is impressed by his sharp suit, easy conversation, and suave confidence. He introduces himself as Charles H. Drouet, a traveling salesman. They chat for nearly the entire train ride, and Drouet, smitten by the pretty girl’s charming innocence, promises to look her up. Carrie gives him her sister’s address, and they plan to meet in a few days.

Minnie meets Carrie at the bustling station. Carrie, despite her sister, feels alone amid the press of the city.

Carrie’s reunion with her sister is uncomplicated by emotions. Minnie’s small and cluttered house is a disappointment to Carrie. Minnie expects Carrie to pay rent once she has found work. Embarrassed by her sister’s house, Carrie writes a letter to Drouet telling him not to visit.