This seminar presents the impact of roofing strategies and urban parameters on microclimate and energy consumption during Chicago's heatwaves. Using regional modeling with updated parameterizations for cool roofs, green roofs, and solar panel roofs integrated into a multilayer building energy model, we find that cool roofs significantly reduce near-surface temperatures and energy demands, achieving cooling energy reductions of 16.6%, 14.0%, and 7.6% respectively, with potential savings of up to 46.7% when utilizing solar energy fully. Additionally, we explore the sensitivity of microclimate to urban parameters like wall conductivity and ground albedo, identifying key factors that influence urban temperatures and energy usage. Results demonstrate that targeted parameters, especially indoor temperature settings and ventilation rates, critically impact building energy consumption. This research underscores the effectiveness of specific urban design modifications in enhancing urban resilience and mitigating heatwave effects, providing valuable insights for climate-adaptive urban planning