Other mistake: When Neal checks his airline ticket it says he departs from N.Y.C. J.F.K. but the movie claims to have him flying out of LaGuardia.
Other mistake: To go from Wichita, KS, to Chicago, they would go NE through KS, Missouri, Illinois. Kentucky is NOT on the route. They are pulled over by Kentucky State Police (Lenny). But this is the trip from Hell. Maybe they took the L O N G way East to Paducah, then back North to Chicago.





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