We investigated the association of grassland birds with field- and landscape-level habitat variables in south-central Wisconsin during 1985–1987. Landscape-level variables were measured and digitized at 200, 400 and 800 m from the perimeter of 38 200 m × 100 m strip transects. A mixture of field and landscape variables was associated with the density of savannah sparrow (Passerculus sandwichensis) and grasshopper sparrow (Ammodramus savannarum). Only landscape variables were associated with the density of bobolink (Dolichonyx oryzivorus), eastern meadowlark (Sturnella magna) and all birds that were grassland species of management concern. Field size was not an important predictor of bird density. Cover-type diversity of the surrounding area was commonly selected in the models for three species and all birds that were grassland species of management concern. Higher bird densities in the transects were associated with landscapes where the cover types were less diverse. Landscapes with low cover type diversity were dominated by grassland, pasture and hay. Field habitat, mean patch size of cover types and distance to woody vegetation were the next most common predictors of avian density. The density of some grassland birds increased as nonlinear woody features such as woodlots and shrub carrs decreased in patch size, decreased in total amount in the landscape and increased in distance from a transect. However, density of other species was positively associated with linear woody features such as the total amount and nearness of hedgerows. The composition of the surrounding landscape, at least out to 800 m, is important in grassland bird management.