To respond the expansion of urban centers, the proliferation of high-rise buildings demands a better understanding of the aerodynamic phenomena around skyway bridges connecting these structures. This analysis, utilizing the advanced computational fluid dynamics verified by wind tunnel test data, investigates the wind characteristics around such bridges, crucial for structural stability, pedestrian comfort, and aerodynamic efficiency. This study focuses on the interactions between a 2 × 2 building array with a building height-to-street width ratio of 30 and a skyway bridge, investigating those factors such as bridge influence, building structures, building height, and bridge position. Using the three-dimensional steady Reynolds-averaged Navier–Stokes equations along with the Reynolds stress model for turbulence closure, the results show that the presence of skyway bridge significantly modifies local wind patterns. Wind speed and turbulence intensity are impacted differently based on the bridge's upstream or downstream settings. Downstream bridges tend to reduce wind speeds due to the sheltering effects, while upstream placement of bridge can enhance wind flow, affecting both the structural design and pedestrian comfort. Additionally, building height variations adjacent to the bridge influence wind velocity and pressure profiles, with taller buildings intensifying wind speeds at lower levels because of the channeling effects. These insights are pivotal for optimizing the skyway bridge designs to improve airflow distribution, enhance environmental sustainability, and ease wind-caused disturbances, offering a guideline for future architectural and urban planning in high-rise districts.