Throughout the novel, Milkman has been weighed down and turned around by his vanity, his selfishness, and his greed. For example, Guitar once asks him, "Looks like everybody's going in the wrong direction but you, don't it?" Milkman finds fault with everyone else and never himself. He literally(albeit accidentally) pees on his sister, Magdalene, because he just does not think about other people. He even faces "backward" when his family goes for drives in his father's Packard, though it "made him uneasy" and feels like "flying blind." He cannot actually "fly," though others in his family could. For most of his life, Milkman is like the white peacock he and Guitar see. Guitar says that it can't fly because it has
Too much tail. All that jewelry weighs it down. Like vanity. Can't nobody fly with all that shit. Wanna fly, you got to give up the shit that weighs you down.
Milkman's own vanity and greed weigh him down. He puts himself first: ahead of his family, ahead of his friends, ahead of Hagar. He even tries to steal from his aunt, Pilate, who is probably the most likable character in the entire novel. Only once Milkman goes in search of the gold he thought she had, a search that takes him to Virginia, does he finally learn what his priorities ought to be.
Milkman learns who "his people" are and where they came from. He learns that he had an ancestor who could fly and who did fly home to Africa after he'd been captured and made a slave. Milkman ruins his nice clothes and shoes, and he even loses his gold watch, slowly shedding those things that would seem to symbolically weigh him down. He even learns to be a generous lover with Sweet and to put someone else first. In the end, then, it makes sense that Milkman learns "what Shalimar knew: If you surrendered to the air, you could ride it." Evidently, Milkman, too, has learned to fly. Given that his ancestor, Shalimar, could fly—as he does in the song that the little children sing—and that Pilate is said to have been able to fly (in a way) as well, this seems hardly surprising (though it is magic). When Pilate dies, Milkman figured out "why he loved her so. Without every leaving the ground, she could fly." If she could be born without a navel, then why not? This is part of the book's magical realism.
Further, it seems that Guitar simply is not meant to fly. In fact, he is always compared to an animal who can only exist on land: a cat. On the very day Milkman is born, Guitar is referred to as a "cat-eyed boy" multiple times. Later, when his grandmother went to ask Macon for an extension on their rent, the narrator says that his "cat eyes were gashes of gold." This description not only ties him to land, but it also ties him to his desire for money, the materialism that develops later in his life. He, too, tries to rob Pilate, and he later attempts to kill Milkman because he believes that Milkman is trying to swindle Guitar out of Guitar's share of the gold. Later, the men Milkman hunts with capture and eviscerate a bobcat (the very one that might have been stalking Milkman at the same time Guitar was doing so). It seems, then, that Guitar is not able to fly because he is too weighed down. His greed restricts him, whereas Milkman's revalued priorities grant him a kind of freedom that Guitar cannot know. This is why he can ride the air, finally, and Guitar cannot.
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