Public perception of local climate forecasts is typically based on data collected from meteorological stations with broad territorial coverage. However, such data may not adequately represent microclimatic conditions at the pedestrian scale—conditions that are crucial for urban design decisions and public health. Thermal perception of individuals, along with local indicators such as temperature, wind, humidity, and solar radiation, can differ significantly from the readings obtained by broad-coverage meteorological stations. This chapter reports the results of research in which we studied microclimatic behavior and its potential influence on urban design. To do so, we explore two places in central areas in Santiago de Chile and demonstrate how fixed meteorological stations, placed at a maximum height of 1.5 m in dense neighborhoods, can yield distinct climatic measurements even when only 270 m apart. Findings identify key factors—including surrounding morphology, vegetation, wind corridors, and solar exposure—that alter microclimates at fine spatial scales. By detecting those factors, the chapter proposes design tools tailored to local microclimatic conditions. Climate-sensitive interventions can improve thermal comfort in public spaces, benefit pedestrians, and help mitigate the impacts of rising extreme temperatures in an era of global climate change.