The Sky View Factor (SVF) is a dimension-reduced representation of urban form and one of the major variables in radiation models that estimate outdoor thermal comfort. Common ways of retrieving SVFs in urban environments include capturing fisheye photographs or creating a digital 3D city or elevation model of the environment. Such techniques have previously been limited due to a lack of imagery or lack of full scale detailed models of urban areas. We developed a web based tool that automatically generates synthetic hemispherical fisheye views from Google Earth at arbitrary spatial resolution and calculates the corresponding SVFs through equiangular projection. SVF results were validated using Google Maps Street View and compared to results from other SVF calculation tools. We generated 5-meter resolution SVF maps for two neighborhoods in Phoenix, Arizona to illustrate fine-scale variations of intra-urban horizon limitations due to urban form and vegetation. To demonstrate the utility of our synthetic fisheye approach for heat stress applications, we automated a radiation model to generate outdoor thermal comfort maps for Arizona State University’s Tempe campus for a hot summer day using synthetic fisheye photos and on-site meteorological data. Model output was tested against mobile transect measurements of the six-directional radiant flux density. Based on the thermal comfort maps, we implemented a pedestrian routing algorithm that is optimized for distance and thermal comfort preferences. Our synthetic fisheye approach can help planners assess urban design and tree planting strategies to maximize thermal comfort outcomes and can support heat hazard mitigation in urban areas.