Synchrony between reproduction and food availability is important in mammals due to the high energetic costs of gestation and lactation. Female polar bears (Ursus maritimus) must accumulate sufficient energy reserves during spring through autumn to produce and nurse cubs during the winter months in snow dens. Adequate time in a den is important to optimize cub development for withstanding harsh Arctic spring conditions and to synchronize emergence with peak prey availability, which occurs in May and June. During 1985–2013, den phenology was investigated using temperature data collected on satellite collars deployed on adult female polar bears in the southern Beaufort Sea (SB) and Chukchi Sea (CS). We examined relationships between den phenology, reproductive success (cub production and post-emergence survival), and environmental factors (weather and sea-ice conditions). Females observed with cubs emerged later and remained in dens on average 15.0 ± 7.6 (SE) days longer than females seen without cubs. Females occupying land-based dens, where estimated snowfall was greater, had higher reproductive success. Recently, female polar bears have increased land-based denning in the SB. Females in CS emerged later from dens than SB females, consistent with better female body condition and higher cub survival in the CS. During years with a greater area of autumn sea ice, reproductive success was higher at land-based versus sea-ice dens, suggesting continued decline in sea ice could negatively affect recruitment. However, further research is needed to better understand mechanistic relationships. Because females emerging later from dens had higher reproductive success, den duration could be a useful metric in population monitoring.