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Advanced Aerial Mobility (AAM) platforms are poised to begin high-density operations in urban areas nationwide. This new category of aviation platforms spans a broad range of sizes, from small package delivery drones to passenger-carrying vehicles. Unlike traditional aircraft, AAM vehicles operate within the urban boundary layer, where large structures, such as buildings, interrupt the flow. This study examines the response of a package delivery drone, a general aviation aircraft, and a passenger-carrying urban air mobility aircraft through an urban wind field generated using Large Eddy Simulations (LES). Since it is burdensome to simulate flight dynamics in real-time using the full-order solution, reduced-order wind models are created. Comparing trajectories for each aircraft platform using full-order or reduced-order solutions reveals little difference; reduced-order wind representations appear sufficient to replicate trajectories as long as the spatiotemporal wind field is represented. However, examining control usage statistics and time histories creates a stark difference between the wind fields, especially for the lower wing-loading package delivery drone where control saturation was encountered. The control saturation occurrences were inconsistent across the full-order and reduced-order winds, advising caution when using reduced-order models for lightly wing-loaded aircraft. The results presented demonstrate the effectiveness of using a simulation environment to evaluate reduced-order models by directly comparing their trajectories and control activity metrics with the full-order model. This evaluation provides designers valuable insights for making informed decisions for disturbance rejection systems. Additionally, the results indicate that using Reynolds-averaged Navier–Stokes (RANS) solutions to represent urban wind fields is inappropriate. It was observed that the mean wind field trajectories fall outside the 95% confidence intervals, a finding consistent with the authors’ previous research.