Mitigating urban heat island (UHI) effects, especially under climate change, is necessary for the promotion of urban sustainability. Shade is one of the most important functions provided by urban trees for mitigating UHI. However, the cooling effect of tree shade has not been adequately investigated. In this study, we used a simple and straightforward method to quantify the spatial and temporal variation of tree shade and examined its effect on land surface temperature (LST). We used the hillshade function in a geographic information system to quantify the spatiotemporal patterns of tree shade by integrating sun location and tree height. Relationships between shade and LST were then compared in two cities, Tampa, Florida and New York City (NYC), New York. We found that: (1) Hillshade function combining the sun location and tree height can accurately capture the spatial and temporal variation of tree shade; (2) Tree shade, particularly at 07:30, has significant cooling effect on LST in Tampa and NYC; and (3) Shade has a stronger cooling effect in Tampa than in NYC, which is most likely due to the differences in the ratio of tree canopy to impervious surface cover, the spatial arrangements of trees and buildings, and their relative heights. Comparing the cooling effects of tree shade in two cities, this study provides important insights for urban planners for UHI mitigation in different cities.