Dreams and dreaming appear throughout the novel as motifs that underscore the memoir's focus on the desires that parents have for their children, the past, and the mythologizing that frequently obscures the truth about important characters in the book.

Obama links the idea of dreams with his father starting in the title of the book. This linkage emphasizes the degree to which Obama's ideas about who he should be as a man emerge from his father's ideas about success. Obama Sr.'s ideas about dreams are ones that emphasize dreams he has for Kenya's modernization and dreams he has that his son will grow up to be of service to his people. Obama's desire to become a community organizer in the African-American community reflect the significant influence of these dreams on Obama's identity.

Obama's ideas about who he should be as a person are also a function of multiple generations of dreams he inherits from the Dunhams. Gramps (and to a lesser extent, Toot) has a dream of an egalitarian, color-blind world in keeping with the goals of the Civil-Rights era of Obama's childhood, while Ann Dunham's dreams reflect the same kind of optimism, augmented with an emphasis on service to others.