In 1889, eighteen-year-old Caroline Meeber boards a train headed for Chicago, leaving behind her small home town of Columbia City. She carries only four dollars, a few paltry belongings, and her sister's address in Chicago.
As the train pulls out of Waukesha, Wisconsin, she becomes aware that a man is observing her. Despite her reserve, she strikes up a conversation with him. The man's name is Charlie Drouet, a traveling salesman, and his flashy clothing and talkative ways make a positive impression on Carrie.
In the course of their conversation, Drouet guesses that she has never been to Chicago; he also learns that she is planning to stay with her sister. He offers to show her around the city. After some hesitation, she gives him her sister's address, and he gives her his card. They make a date for the following Monday. Drouet offers to carry her bags for her, but Carrie decides that she should be alone when she meets her sister. Drouet cheerfully acquiesces to her demands, offering to wait at a distance until he sees her meet her sister. Carrie agrees, surprised and grateful that someone would be so considerate of her safety. When the train arrives in Chicago, Carrie's sister Minnie is waiting for her at the station.
Minnie introduces Carrie to her taciturn husband, Hanson, when they reach her apartment. Hanson is mostly indifferent to Carrie's presence, but he remarks that she should find work easily in Chicago. Carrie studies the apartment and quickly determines that Minnie, Hanson, and their infant son live a narrow, lean existence. Hanson goes to bed early because he has to wake up for work before five in the morning. Carrie decides that it would be inappropriate for Drouet to visit her at the apartment, so she writes him a letter, instructing him to wait until he hears from her again.
The next day, Carrie walks to the wholesale district to look for work. Shy and fearful, she cannot bring herself to ask for a job at most of the places she passes. After a while, she works up the courage to inquire at a few stores. The owners are alternately kind and cold, but none of them offer her a job. One man suggests that she try to get a job as a shop girl in one of the department stores, but Carrie discovers that the stores are only looking for people with experience. Carrie feels ashamed when she compares her worn clothing to the sharp, neat apparel of the other applicants. Walking through the department store, she longs to buy the clothing and trinkets on display. Eventually, she finds a job in a shoe factory, where she earns four and a half dollars a week.
Hanson and Minnie are pleased that Carrie has found work so quickly, but Hanson interrupts Carrie's wild dreams of the buying power of her wage when he asks if she will have to spend any on car fare. They suggest a tour of the city over the weekend, and Carrie immediately recognizes their emphasis on free amusements. Carrie is eager to go to the theater, but she senses disapproval from Minnie and Hanson when she mentions the idea. They expect her to pay for the food she eats at their apartment, and her notions of spending money on entertainment run counter to their plans to profit from her stay in Chicago. Carrie goes downstairs to sit on the stoop.