Overwintering is a key demographic stage for migratory birds but remains poorly understood, especially among multiple declining grassland bird species. The non-breeding ranges all 4 species of longspur (i.e., chestnut-collared [Calcarius ornatus], Smith's [C. pictus], Lapland [C. lapponicus], thick-billed [Rhynchophanes mccownii]) overlap in Oklahoma and the Texas Panhandle, USA, making this region ideal to study their wintering ecology. We evaluated the relationship between wintering longspur occurrence and fine-scale habitat characteristics using a combination of standardized bird surveys and vegetation plot sampling. Our study encompassed large, representative tracts of 3 prairie ecosystems (i.e., shortgrass, mixed-grass, and tallgrass prairies) that intersect within the Southern Great Plains, during winters of 2018-2019 and 2019-2020. Using randomization tests and classification trees, we characterized longspur habitats and compared these associations across the 3 prairie ecosystems. Fine-scale winter habitats (horizontal structure, vertical structure, and species compositions) varied among all 4 longspur species, varied at very fine scales, and differed between grassland types. Our findings can be applied to the management of grasslands such as decreasing vegetation height in mixed-grass prairies for chestnut-collared longspurs or removing woody vegetation in shortgrass prairies for thick-billed longspurs to help develop full-life cycle conservation for longspurs, which have experienced population declines.