Migration detours, the spatial deviation from the shortest route, are a widespread phenomenon in migratory species, especially if barriers must be crossed. Moving longer distances causes additional efforts in energy and time, and to be adaptive, this should be counterbalanced by favorable condition en route. We compared migration patterns of nightingales that travelled along different flyways from their European breeding sites to the African nonbreeding sites. We tested for deviations from shortest routes and related the observed and expected routes to the habitat availability at ground during autumn and spring migration. All individuals flew detours of varying extent. Detours were largest and seasonally consistent in western flyway birds, whereas birds on the central and eastern flyways showed less detours during autumn migration, but large detours during spring migration (eastern flyway birds). Neither migration durations nor the time of arrival at destination were related to the lengths of detours. Arrival at the breeding site was nearly synchronous in birds flying different detours. Flying detours increased the potential availability of suitable broad-scale habitats en route only along the western flyway. Habitat availability on observed routes remained similar or even decreased for individuals flying detours on the central or the eastern flyway as compared to shortest routes. Thus, broad-scale habitat distribution may partially explain detour performance, but the weak detour-habitat association along central and eastern flyways suggests that other factors shape detour extent regionally. Prime candidate factors are the distribution of small suitable habitat patches at local scale as well as winds specific for the region and altitude.