With an increasing awareness of urban health and well-being, this study highlights the growing importance of considering environmental quality in urban design beyond mere energy performance. This study integrates outdoor and indoor quality by investigating the effect of design parameters at an urban block scale (building form restricted to width and length as rectangular and square, building orientation, block orientation, building combination, building height, facade length, built-up percentage, setbacks, and canyon aspect ratio) on outdoor thermal comfort and energy use intensity. In addition, it explains the different correlations between outdoor thermal comfort and energy use intensity in different urban block designs in a hot-summer Mediterranean climate in Jordan. The study adopts a performance-driven approach using simulation tools of Ladybug, Honeybee, Dragonfly, and Eddy3d plugins across the grasshopper interface and evaluates 59 different urban block designs with nine different orientations (0°, 1°, 45°, 85°, 87°, 90°, 355°, 358°, and 359°). The results show that there is a positive correlation between the canyon aspect ratio and the environmental performance of the urban block designs. North–south street canyons are more effective at enhancing microclimates. Negatively increasing the street aspect ratio by more than four affected outdoor thermal comfort by increasing longwave radiation. Further results suggest a positive correlation between the compactness of urban blocks and their environmental performance, with north–south street canyons found to be more effective in enhancing microclimates. The study emphasizes the need to understand the distribution of open spaces formed by buildings and to strike a balance between day and night, as well as summer and winter conditions in outdoor spaces.