Tallgrass prairies are among the most threatened ecosystems in the world. Remaining prairies tend to be small and isolated and many are associated with urban and suburban landscapes. We asked how urbanization might impact the conservation value of tallgrass prairie fragments for grassland birds by comparing the densities and the probability of occurrence of Dickcissels (Spiza americana), Grasshopper Sparrows (Ammodramus savannarum), and Eastern Meadowlarks (Sturnella magna) across 28 grasslands surrounded by low, moderate, and high levels of urbanization. We employed a hierarchical model selection approach to ask how variables that describe the vegetation structure, size and shape of grasslands, and urbanization category might explain variation in density and occurrence over two breeding seasons. Occurrence of all three species was explained by a combination of vegetation and patch characteristics, though each species was influenced by different variables and only Eastern Meadowlark occurrence was explained by urbanization. Abundance of all three species was negatively impacted by urbanization, though vegetation variables were also prevalent in the best‐supported models. We found no evidence that vegetation structure or other patch characteristics varied in a systematic way across urbanization categories. Although our results suggest that grassland bird density declines with urbanization, urban tallgrass prairies still retain conservation value for grassland birds because of the limited availability of tallgrass prairie habitat and the limited impact of urbanization on species occurrence.