The bus trip brings Sal to windy Chicago and he gets a room at the YMCA. He wanders around Chicago and then takes a bus to Joliet, Illinois. By this point, he has spent more than half of his money. He hitches a ride on a dynamite truck. After this ride ends, he hitches a ride with a woman who has him drive to Iowa, even though he doesn't have a license. He crosses the Mississippi at Davenport and gets out of the car. He walks around for awhile as the sun sets. The woman drives away in a different direction. A man gives him a ride back into the city where he takes a bus to a gas station and hitches a ride with a trucker. The driver doesn't talk and Sal is relieved because "one of the biggest troubles of hitchhiking is having to talk to innumerable people, make them feel that they didn't make a mistake picking you." Part 1, Chapter 3, pg. 16. The driver yells a few short anecdotes above the roar of the truck. When it is time for them to part ways, he signals a truck behind him and Sal gets another ride with a different trucker. This driver is crazy. They stop outside Iowa City to sleep and leave again at dawn. Sal gets out at Des Moines, goes to town, and stays in a hotel for the night because the YMCA was filled up.

"I woke up as the sun was reddening; and that was the one distinct time in my life, the strangest moment of all, when I didn't know who I was- I was far away from home, haunted and tired with travel, in a cheap hotel room I'd never seen, hearing the hiss of steam outside and the creak of the old wood of the hotel, and footsteps upstairs, and all the sad sounds, and I looked at the cracked high ceiling and really didn't know who I was for about fifteen strange seconds." Part 1, Chapter 3, pg. 17

Sal gets up the next morning and eats apple pie and ice cream for the first of many times. He yearns to get to Denver where all his friends are waiting. He receives a series of rides up the road and meets another New York hitchhiker named Eddie. Eddie looks bad, but Sal sticks with him anyway just to have a companion. They get a ride only to get stranded in Stuart, Iowa, where they get drunk and take a bus the next day. Sal pays for Eddie's fare. In Omaha, Sal is excited because he sees his first real cowboy. In Missouri, they meet another cowboy who needs a car driven into Montana. Sal rides with the cowboy and Eddie drives the car. Eddie drives really fast, as if he is going to steal the car, but the cowboy keeps up with his pace. The cowboy talks about how he used to hop freight trains once a month. He is leaving Nebraska to settle in Montana. Sal and Eddie end up in Grand Island and resume hitchhiking. One ride from young people and one with an old man brings them to Shelton. Eddie realizes that he was in Shelton before when he was in the Army, and he didn't like it then. They get stranded in the cold rain. Sal gives Eddie a wool shirt. He sends a postcard to his aunt. A man drives up in an expensive car; they think he is the sheriff, but he is actually a carnival owner trying to get them to join his show. Sal replies that he's moving quickly and doesn't have the time. Eddie agrees and the man leaves. Sal refers to Eddie as his "pal of the road"
Topic Tracking: Generosity 2