Extreme heat events are becoming more frequent and intense. In cities, this problem is often intensified by the presence of the urban heat island (UHI). This presents major challenges to reduce adverse health effects of hot weather, particularly in vulnerable populations. Here we explore the impacts of increasing residential air conditioning (AC) adoption as an adaptive measure to extreme heat, with New York City (NYC) as a case study. This study uses AC adoption data from New York City Housing and Vacancy Surveys to study impacts to indoor heat exposure, energy demand, and UHI. The Weather Research and Forecasting (WRF) model, coupled with a multi-layer building environment parameterization and building energy model (BEP-BEM) is used to perform this analysis. The BEP-BEM schemes are modified to account for partial AC use and used to analyze current and full AC adoption scenarios. A city-scale case study is performed over the summer months of June – August 2018, which includes three different extreme heat events. Simulation results show good agreement with surface weather stations. Results show that increasing AC systems to 100% usage across NYC results in a peak energy demand increase of 20%, while the UHI slightly increases on average by 0.42 °C. Results highlight potential tradeoffs in extreme heat adaptation strategies for cities, which may be necessary in the context of increasing extreme heat events.