Projected increases in the variability of both temperature and precipitation will result in the greater likelihood and magnitude of extreme weather (e.g., cold snaps, droughts, heat waves) with potential implications for animal populations. Despite the ecological consequences of extreme weather, there are several challenges in identifying extreme events and measuring their influence on key demographic processes in free-living animals. First, there is often a mismatch between the spatial and/or temporal resolution of biological and climate data, masking the ability to draw inferences about how species and populations respond to extreme events. Second, there are multiple approaches for identifying an extreme event ranging from statistical definitions (e.g., standardized deviates) to species-specific biological thresholds. Lastly, the impacts of extreme weather on species can vary as a function of differences in exposure and intrinsic sensitivity to climate variability. In the Northern Hemisphere, rapid warming has contributed to a “wobblier” jet stream that promotes the higher likelihood of unusually cold Artic air moving southward and leading to more extreme winter conditions. Due to these conditions, the Upper Midwest experienced two of the coldest winters in the past 35 years during 2014 and 2015. We combined radiofrequency identification technologies with fine-scale weather data and standard capture-mark-recapture analyses to estimate weekly and overwinter survival rates of a common winter passerine, the black-capped chickadee (Poecile atricapillus), in a near continuous fashion. Using both statistical and biological definitions of weather extremes, we found that declining ambient temperatures reduced survival (despite the presence of favorable microclimates), and that biologically-defined thresholds of extreme weather were better at explaining variation in survival than statistical ones. Moreover, habitat fragmentation interacted with temperature to modify the exposure of birds to extreme weather with survival consequences, but sensitivity, as measured by body condition, did not appear to play a significant role. These results provide a novel contribution to the understanding of how extreme weather may interact with local- and landscape features to influence the demography of species and populations, and suggest potential opportunities for climate change adaptation in human-dominated landscapes