In Chapter Twenty-Six, Carrie thinks through her current situation and knows she will have to leave her flat soon. She has only seven dollars and does not want to ask Hurstwood for help.
Drouet is staying at the Palmer House and is initially angry with Carrie, but then begins to hope she will contact him. Meanwhile, she tries to allay her fears for the future by looking for work in the business district. On Monday, she goes to theatres as she considers making her living by acting on the professional stage, but is too overawed to ask. By Tuesday she is feeling braver and a theater manager informs her she would have a better chance of work in New York. He then begins to flirt with her and says she could join a chorus line. She leaves after declining his offer for lunch. He tells his companion she would never make an actress; to him, she is just another chorus girl.
She picks up her mail at the post office. A letter from Hurstwood makes her decide to write to him to let him know she has been told of his marriage and to break off their relationship. She then attempts to find work in department stores and is treated with more consideration than when she first came to Chicago (as she is dressed more stylishly), but is told it is the quiet season. After finding no feasible work, she decides to pawn her trinkets and returns homes. She notes that Drouet has taken some of his possessions whilst she has been out and presumes he is determined to stay away. She does not know that he came to patch their relationship up and wants to return tomorrow to see her.
Hurstwood receives Carrie’s letter in Chapter Twenty-Seven and finds solace in the fact that she has written to him (rather than in what she says). He sees Drouet at the Palmer House and discovers he is there alone. This inspires Hurstwood to visit Carrie, but she has already left for the theater when he gets there.
After drinking with friends, Hurstwood checks the saloon safe as he does every night and finds it is unlocked. He spots bundles of money which he estimates to amount to 10,000 dollars. Slightly inebriated, he takes the money out and thinks of stealing it so he can live with Carrie, and then returns it to the safe. He continues to waver and removes it once more to put it into his satchel. He returns it to the incorrect place and removes it yet again. He feels his decision is made when the lock of the safe clicks shut whilst the money is out of it. The narrative forcefully argues that this is a crime of chance - and refuses to condemn Hurstwood morally for his actions. His wavering is used to demonstrate that he, and other perceived criminals, do have a conscience, but circumstances dictate the choice he lives to regret. He decides to catch a train for Detroit, then Canada, and wants to take Carrie with him. On arriving at her home, he asks the maid to fetch Mrs Drouet as her husband has been injured and is in the hospital. When Carrie comes to the door, he repeats his story and she gets into the cab with him. He quietly asks to be driven to Michigan Central Depot.
To cover his actions, Hurstwood tells her in Chapter Twenty-Eight that they have to get a train as Drouet is way out on the South Side. He buys tickets for Detroit without telling her the truth and gets her on board. After half an hour of travelling, he admits that they are not going to see Drouet. She is angry and wants to be let off the train, and he is worried about her attracting attention. He persists in persuading her that he loves her and wants to be with her. He also explains that they can go to Montreal, or New York. This proposition interests her, but she tries not to show it. However, she does not alight at the first stop and so decides to remain with him.
Hurstwood is pleased that he has managed to mollify Carrie, but then begins to worry again about the theft and the thought of living in exile. At Detroit they quickly catch the Montreal connection and he is relieved to see no policemen.
In Chapter Twenty-Nine, they arrive in Montreal and Hurstwood books Carrie’s room under the name Murdock. She is still angry and tells him he had no right to care for her, but still wants to marry him for security. He agrees, saying they will that day.
He calls at a barbershop and is recognized by an acquaintance from Chicago. When he returns to the hotel he feels as though he is being watched. His fear of repercussions for his actions mounts when he checks the newspapers to see if he has been reported, and sees a small mention of his crime. He wishes he could undo it all, but cannot think of a way out now that he has taken the money.
When he visits Carrie in her room, there is a knock at the door and he answers. It is a detective sent to find Hurstwood and he talks to him away from the room so Carrie cannot hear their conversation. The detective advises him to give up the money and Hurstwood tells him he does not even want it. Hurstwood informs him he will write to his bosses and sort it out. The troubled state of his mind can be seen in the letter he secretly writes to them. He says he will return the majority of the money and will pay the rest back later. He also asks if there is a chance of his job being restored.
He then turns his attentions back to Carrie and asks her to marry him again. He suggests they could marry under a new name, Murdock, but she says she prefers Wheeler. He gets the license and they marry under this name. He telegraphs his bosses, after receiving a letter from them agreeing to let him repay the money, and he pays their representative 9,500 dollars and retains 1,300.
The chapter ends with Hurstwood and Carrie leaving for New York. He is relieved to see no police waiting for him at Grand Central Station, and she is still oblivious about his fears (and theft). She demonstrates that she is beginning to have opinions of her own when she criticizes New York on her first glimpse of it.
Chapter Thirty commences with a description of New York and how there is a sharp contrast between the wealthy and the rest of the populace. There is a negative effect of such obvious wealth, as it sets up a craving in people to achieve the same. Hurstwood begins to feel increasingly out of place as he is used to spending five times the amount of money he has in a year.
They find a flat for 35 dollars a week and Hurstwood eventually manages to buy into a saloon business. He prefers his former position in Chicago, though, and misses his male friends. Carrie notices he is not as ‘easy’ as he used to be and his wardrobe is limited. He is unhappy as he constantly compares his old life with this new one and is afraid to bump into old acquaintances after an awkward encounter.
These crucial chapters lay out the crime Hurstwood lives to regret. He does not even consider himself to be a thief as his act of taking the money was not pre-planned or thought through. He is described as making the wrong decision at the time, and is punished for this through exile and later self-destruction. Through Hurstwood’s characterization, it is possible to see the unpicking of received moral values which see the world as black and white, or good and evil. Hurstwood’s constant wavering between what to do for the best (for himself, admittedly) has the effect of undermining the notion that all criminals are evil. This may be compared similarly to the portrayal of Carrie, who, as the supposed fallen woman, should be traditionally seen in a negative light; however, Dreiser also refuses to condemn her.
Sister Carrie: Chapters 26-30