Agriculture and wildlife conservation programs have converted vast amounts of cropland into grasslands planted with exotic species. Understanding how landscape context influences avian use of native and planted grasslands is essential for developing effective conservation strategies in agricultural landscapes. Our primary objective was to determine the extent to which the amount and type of grassland in the surrounding landscape influences the abundance of grassland songbird species on native and planted grassland parcels in southern Saskatchewan and Alberta, Canada. Bird abundance was more strongly influenced by the amount and type of grassland within 400 m of breeding parcels than at larger spatial scales. Grassland specialists responded similarly to habitat and landscape type over both years and provinces. Sprague's pipit (Anthus spragueii) and Baird's sparrow (Ammodramus bairdii) were most common in native grassland parcels surrounded by native grassland and were more likely to occur in planted grasslands surrounded by native grassland. Bobolinks (Dolichonyx oryzivorus) were most common in planted grassland parcels, but their abundance increased with the amount of native grassland surrounding these parcels. Our findings indicate that the suitability of planted grasslands for these species is influenced by their proximity to native grassland. Grassland generalists showed mixed responses to habitat and landscape type over the 2 years (Le Conte's sparrow [Ammodramus leconteii]) and between provinces (Savannah sparrow [Passerculus sandwichensis] and western meadowlark [Sturnella neglecta]). Management to benefit grassland specialists should therefore consider the landscape context when seeding cultivated land to non-native grassland and conserve extant native grassland.