Less than a paragraph later, we're in Chicago; less than a page later, the narrator is hitching west after kicking himself for spending money on a bus from Chi-town to Joliet. The way he brushes off both trips is a clear indication that the Road of the book's title is not buses and paid fares, it's hitchhiking and the pricelessness of freedom.
Along the way he sees "my beloved Mississippi River." Beloved why? What for? Because he's read about it in a Mark Twain novel? Seen it dozens of times before? It's an odd use of the adjective, it implies a past which is never revealed, and points up the fact that there's very little of the narrator's past that is part of this story. Maybe we'll get it along the way, but if we don't, it's because it's not necessary; almost like he's filling it in when and if he needs it, like an oil change at a gas station.
Stuck in Davenport, he tries to get out and winds up right back where he started, like a miniature version of the last chapter. The Road is a place of fits and starts, of deep frustrations and high joys (the narrator would probably say "holy joys"). After a couple of truck drivers get him to Iowa, where he can "see Denver looming ahead of me like the Promised Land," we get a flash-forward: he's in a town "where years later Dean and I were stopped on suspicion in what looked like a stolen Cadillac." It's the first mention of Dean in a while, and the first time he's explicitly situated in the future, like Denver.
For the rest of the chapter, the narrator (still nameless) hooks up with a hitcher from New York named Eddie, who may be on the run from something. It's yet another rule of The Road: the Road is only home to two kinds of people, those who are running towards something they can't describe and those who are running away from something they don't want to talk about.
In this section, there's another little miniature, as a cowboy tells the guys a story about hopping freight trains back in the day, and another fits and starts moment when they end up in Shelton, Nebraska, where Eddie was years ago. In the ensuing drizzle (the rain is starting to become symbolic; it always seems to happen when there are no rides out of town), the narrator gives Eddie his wool plaid shirt to help keep him warm, a gift that he later regrets when Eddie without a word or a backward glance hops onto a trailer with only room for one passenger, leaving the narrator stuck in Shelton.
But before Eddie vanishes off towards the horizon, he and the narrator are offered a job with a travelling carnival. It's tempting; if there's one group of people that could actually form the kind of rootless community which could survive on The Road, it's carny folk. It's like a myth within a myth, and here's the opportunity to take it, but they pass. You get the sense that they pass not just because it's a job, but because it's a job where you have to deal with normal people whenever you stop moving and pitch your tent. And if you're going to deal with normal people in town after town, why not just settle down in one? Which is not the pearl you want The Road to hand you. Just another empty oyster.