Recent advances have revealed that female birdsong is widespread and multifunctional. Female song was likely ancestral among songbirds and persists in many lineages today. Nevertheless, many species lack female song, and researchers are interested in understanding the selective factors that promote and counter the persistence of this trait. Female song is associated with life-history traits including year-round territoriality, non-migratory behavior, sexual monochromatism, and monogamy. Most studies examining these relationships have looked at clades with a migratory ancestor and have found that gains of migratory behavior are strongly correlated with losses of female song (and duetting). Here, we ask if the reverse pattern exists: in a large clade of songbirds with a migratory ancestor, do losses of migratory behavior correlate with gains of female song and visual signaling traits? We investigated correlations between female song, migration, and dichromatism in 107 species of New World Warblers (Family Parulidae). All of these species are predominantly monogamous and territorial when breeding, 50 (47%) are migratory, 49 (46%) are monochromatic, and 25 (23%) show female song. On a robust genetic phylogeny maximum likelihood methods recover migration and monochromatism as the ancestral state in warblers. Female song is generally not reconstructed as present in any deep nodes of the phylogeny, suggesting that most extant species with female song evolved this trait independently and relatively recently. Gains of female song do not correlate with losses of migration. Losses of dichromatism do correlate with losses of migration. Thus, in this clade, visual signals are associated with sedentary vs. migratory lifestyles, but female acoustic signals are not. Our results show a different pattern from that seen in similar studies and support the hypothesis that losses, but not gains, of female song are driven by life history.