Natural small, xeric hill prairies in forested landscapes throughout the Midwest United States often contain high diversity and unique species of some organisms because of their unusual landscape context and microclimate. We measured the diversity, richness, and abundance of the bee communities of five hill prairies located in northeastern Iowa and we compared these to values for large prairie preserves in northwestern Iowa, using a Monte Carlo resampling approach to standardize sampling effort between habitat types. We also measured the diversity and richness of the flowering forb communities at the hill prairies and we quantified percentage of the landscape at a 1 km radius in different landscape elements. Bee diversity at the five hill prairies spanned the range of diversity values for large prairies preserves, so although the hill prairies are small (<5 ha), their bee communities are not uniformly depauparate compared to larger western prairie preserves. Bee diversity was significantly related to flowering forb diversity, and may have been influenced by landscape features within 1 km—particularly the percentage of agricultural row crops and open water, which may negatively affect bee diversity at the sites. Iowa’s hill prairie bee communities were largely composed of widespread eastern species, although about 10% of the bee species have more northern or western ranges and appear to be taking advantage of the region’s unique habitat features. Given the dependence of the bee communities on the plant diversity of the sites, management of the plant community to maintain its diversity will also likely benefit bee diversity.