After receiving Carrie's letter, Drouet puts thoughts of her aside. He goes to Fitzgerald and Moy's, an upscale saloon frequented by the Chicago's upper class, to pass the evening. Drouet is on friendly terms with George Hurstwood, the manager of the saloon, who rubs elbows with the important businessmen, politicians, and actors of Chicago. Drouet and Hurstwood chat about Drouet's employers and his latest trip. Drouet mentions that he "struck a little peach"--that is, met Carrie--"coming in on the train Friday."
Back at the apartment, Carrie irritates Hanson by informing him and Minnie that she hates her job. Carrie is disappointed that they offer no sympathy. Her board costs four dollars a week, and she has already seen enough to know that living with them will be gloomy and plodding. After dinner, she goes outside to stand on the stoop. This displeases Hanson, and he tells Minnie that her behavior looks bad. Carrie comes to realize that, after deducting the cost of living with Minnie and Hanson from her wage, she will not even be able to afford car fare.
Carrie's second day at work is just as bad as the first. She thinks the other women are too common in their dress and their use of slang. Moreover, she dislikes the fact that they act so freely with the men in the factory. It bothers her that the men think that she is just like the other women; men on the street seem to be just as free with her. During the weekend, Minnie and Hanson take her to Garfield park, but Carrie is unhappy because she does not "look well enough." On Monday, she listens to the other women talk about their happy weekends with young men who took them out on the town. Carrie despairs at ever having enough money to have the things she wants.
Winter arrives, and Carrie needs warmer clothing. Minnie allows her to keep some of her earnings for a hat. Carrie becomes too ill to work, so she loses her job. Hanson suggests that she go back home. During the fourth day of her unsuccessful search for another job, Carrie encounters Drouet on the street. He takes her to lunch. The high prices at the restaurant dismay Carrie, but Drouet orders a large meal for both of them. He learns that she has been ill and that she has been trying for several days to find another job. She states that she will probably have to leave Chicago and return home. She reluctantly accepts twenty dollars from Drouet to tide her over. He tells her to buy some new clothes and meet him for a matinee show the next day.
Walking home, Carrie realizes she cannot buy clothing because she will have to explain to Minnie and Hanson where she got the money to pay for it. She resolves to return the money to Drouet. However, when they meet the next day he takes her to buy the clothing despite her protests. He also offers to rent a room for her so she can leave Minnie and Hanson's flat. She returns to the apartment and leaves a note for Minnie stating that she is going to live elsewhere in the city. Afterward, she leaves to meet Drouet under the pretense of going downstairs to stand on the stoop as usual.
Carrie wonders anxiously whether she will be able to get a job. For several days, Drouet takes her out sight-seeing, to the theater, and out to eat. Her misgivings about leaving Minnie and Hanson are swept away. Minnie has a troubled dream that Carrie is slipping away from her toward some unknown danger. Drouet invites Hurstwood to his home one evening for a game of cards, wanting to introduce Hurstwood to Carrie because she has moved in with him.