Aerial insectivorous birds have experienced alarming population declines in eastern North America. Meanwhile, urbanization continues to increase rapidly, with urban land use comprising 69.4 million acres, or 3.6% of total land area, in the contiguous United States. Multiple environmental changes are associated with urbanization, including alterations to local climate, changes in habitat structure, and potential shifts in both terrestrial and emergent aquatic flying insects on which aerial insectivorous birds rely. Here, we investigated the linkages between urbanization, water quality, and Tree Swallow (Tachycineta bicolor) reproductive success and body condition at seven river-riparian sites representing urban and protected land use in Columbus, Ohio over five consecutive years (2014-2018). Tree Swallows at urban and protected sites relied on emergent aquatic insects for 37.4 and 30.8% (SD = 28.4 and 24.1%) of their nutritional subsidies, respectively. Despite the loss of environmental quality generally attributed to cities, Tree Swallows exhibited greater reproductive success in urban settings where climate was more amenable to egg and nestling survival, and the breeding season was longer. Urban-nesting Tree Swallows initiated laying 7.9 days earlier and fledged 35% more young per nest than those at protected sites. Multiple characteristics of urban sites appeared to drive these patterns, including differences in mean and extreme air temperatures and measures of water quality (e.g., water temperature, nutrient concentrations, turbidity). However, chronic effects of elevated Hg concentrations – which were 482% greater in adult swallow blood at urban sites than at protected sites where swallows exhibited a 17.4% lower trophic position – may disadvantage individuals in other ways. Further, although Tree Swallows are a good model aerial insectivore bird species, characteristics of urban landscapes that benefit Tree Swallows may not advantage other aerial insectivorous birds owing to differences in life-history and foraging strategies. These findings implicate urbanization, local climate, and water quality as important considerations in the conservation of aerial insectivorous birds.