Plot hole: After the car burns, and they arrive at the motel, Neal only has $17.00 on him and nothing but melted credit cards, forcing him to give up his watch to help pay for the room. Del only has $2.00 but his watch doesn't quite flip the bill. At this point, between Neal and Del, they only have $2.00. However, when Neal invites Del into the room, so he doesn't freeze to death, they are eating Doritos and drinking shooters. Even in 1987 Doritos and a bunch of shooters must have cost more than $2.00. This is assuming Del didn't already have them in his trunk. But even if he did, at the end, Neal gets on his train, makes a return trip to find Del just where he thought he'd be, and then they'd both have to get back onto that train. After all, they both showed up at Neal's home. Once again, It would take money to get on that train. Four train fares with only $2.00. Neal's first trip, return trip, and Neal with Del for the last trip = four fares.
Planes, Trains & Automobiles (1987)
1 plot hole
Directed by: John Hughes
Starring: Kevin Bacon, Steve Martin, John Candy, Michael McKean, Laila Robins
Continuity mistake: When John Candy is singing "The Mess Around" in the car, the car swerves, and a hubcap from the passenger side rolls off. The hubcap is back on in the next scene. (00:57:20 - 00:58:50)
Del: You could kill a man like that, hitting him in the stomach. That's how Houdini died you know.
Trivia: In the scene after the plane lands in Wichita, Kansas, when the announcer comes over the loudspeaker look at the destination on the flight info display. It says "nowhere".
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Answer: He's not homeless, he has a house or an apartment somewhere, or lives out of hotels. He just no longer has a 'home', ie, a place where he's happy and someone loves him.
Brian Katcher