The evolution of long-distance migratory behavior from sedentary populations is a central problem in studies of animal migration. Three crucial issues that remain unresolved are: (1) the biotic and abiotic factors promoting evolution of migratory behavior, (2) the geographic origin of ancestral sedentary populations, and (3) the time scale over which migration evolves. We test the role of postglacial population expansions during the Quaternary in driving the evolution of songbird migration against prevailing views favoring the role of intraspecific competition. In contrast to previous attempts to investigate these questions using interspecific phylogenies, we adopt an intraspecific approach and examine the phylogeography of a North American songbird, the chipping sparrow (Spizella passerina), which exhibits both long-distance migratory behavior in temperate North America and sedentary behavior in Mexico and Central America. We show that migratory populations descend from sedentary populations in southern Mexico and that migration has evolved as a result of a northward population expansion into temperate North America since the last glacial maximum 18,000 years ago. Migration appears to have evolved rapidly in some species as populations colonized areas of high seasonality in the temperate zone. The phylogeography of the yellow-eyed junco (Junco phaeonotus), a strictly sedentary species, provides a null model supporting the view that northward range expansions were driven solely by environmental factors and not by a predisposition to evolve migratory behavior. These results provide the strongest evidence to date that historical climate patterns can drive the rapid evolution of avian migration in natural populations, and they suggest a general mechanism for the repeated evolution of migration within and across bird lineages.