Urbanization is rapidly reshaping global cities, influencing local climates, and altering urban thermal environments. This chapter explores the role of urban morphology and street-level solar radiation in regulating urban climate, with a particular focus on high-density environments. Compact urban structures impact energy consumption, human comfort, and ecological balance, making precise assessment crucial for sustainable urban planning. Using Google Street View (GSV) imagery, this study develops a cost-effective and scalable method to quantify urban street canyon morphology and solar radiation. It integrates machine learning and spatial analysis to extract sky openness, tree canopy, and building density, offering a refined approach to urban thermal assessment. The findings enhance our understanding of street-level solar exposure and its implications for thermal comfort, health risks, and energy efficiency. The study provides valuable insights for urban policymakers, aiding the development of climate-responsive planning strategies to mitigate urban heat stress while ensuring adequate sunlight access in high-density cities.