Dean speeds across Nebraska, Iowa, Illinois. He tells Sal more stories about when he was a teenager: running to Los Angeles, stealing cars, falsifying his age to get work, being in and out of jail, and going to Denver, where he met Marylou, who was fifteen then. Seeing bums by the side of the railroad tracks makes him think of his father. He and Sal dream about driving around the whole world in the Cadillac. When it is day again, Dean is driving so fast and crazily-sometimes passing six cars at a time-that Sal can't stand it and has to go into the backseat. Dean gets in a minor accident, bumping the car ahead at 5 mph, and they are briefly taken in to the police station. Everyone thinks the car is stolen, but they straighten it out with the owner in Chicago and go on, picking up two hobos on the way. Illinois small-town people come out to look at them suspiciously when they stop for gas. Sal imagines that they look like a suave gang of California desperados coming to take on the Chicago gangs. When they get to Chicago, they have come from Denver in seventeen hours of driving, an average of 70 mph (Remember, this is 1949!).
They drop off the hobos and the students, clean up a bit, and then hit the jazz clubs of Chicago. Sal describes the recent history of bop and jazz: Louis Armstrong, Charlie Parker, Thelonius Monk, Lester Young . . . Now there are all kinds of types playing in Chicago. They see "God" again--the blind pianist George Shearing, who gives an awesome performance. They listen to the musicians play all night. In the morning, everyone staggers home, and Sal and Dean return the battered Cadillac to the owner's garage, leaving quickly, before anyone sees what bad shape the car is in.
They take a bus to Detroit. Dean sleeps and Sal talks to a pretty but dull country girl who tells him joylessly about making popcorn on the porch in the evenings. In Detroit, low on money, Sal and Dean go to the all-night movies on Skid Row and watch a cowboy movie and a movie about Istanbul over and over. Sal is dead asleep for a while, and later Dean tells him that he was almost swept away by the theater cleaners. Sal speculates on what it would be like if he were swept away and lost in the garbage. In the morning, after going to some bars and trying to pick up girls without success, they go to the travel bureau and get a ride to New York with a nice blond man.
Back in New York, they stay at Sal's aunt's new flat in Long Island. She says Dean can stay for a few days only. Dean and Sal promise each other to be friends forever. At a party in New York one night, Dean meets Inez. Shortly, he wants to divorce Camille and marry Inez. A few months later, Camille gives birth to Dean's second baby, and then Inez has a baby too. Dean is penniless and busy with his usual joys and troubles, so he and Sal don't go on to Italy after all.
As the road represents the thrill of movement, the car represents Sal and Dean's dream of freedom; Dean imagines that they could drive anywhere in the world. Sal says that Dean's "soul" is wrapped up in a car, a coast to reach, and a woman at the end of the road. It is an exhilaration of anonymity and ambiguity, fueled not by wandering aimlessly, but by the idea of speeding toward a new future: an ideal woman waiting, a place where all of their problems will be magically solved. Everything, include themselves, can be remade while on the road. Just as they can imagine their destination to be ideal, they can act as their ideal selves. Sal loves picturing Dean and himself as desperados, California outlaws. To the people they pass, they could be anyone. Whenever they get to the end of the road and can't go any further--hitting the Pacific or the Atlantic--they have to face the specifics of their lives, and often feel at a loss to do so.
Jazz, exploding across the country at this time, figures prominently in their night in Chicago. To Sal, the sound of a saxophone is as "lonely as America." The music embodies Sal and Dean's thoughts and emotions: eruptions of sound both joyous and melancholy, frenetic and slow, improvised solos. They are voices from the fringe speaking for a new era, apart from the old structures. Melodies are found and lost, found again, and lost again.
On the bus to Detroit, it becomes clear that that Sal is not speaking just for himself and Dean, but for a whole time and generation. The country girl he talks to on the bus, like everyone else, doesn't know what she wants. In Detroit, in the seedy all-night theater, they are surrounded by people who have "nothing to do, nowhere to go, nobody to believe in." Sal's sense of spiritual malaise seems to be a product of an entire culture.