The urban wind environment is characterized by complex flow structures and high levels of turbulence due to the densely built up regions and the presence of tall buildings. This renders the flight operations in urban areas challenging since the turbulent airflow characteristics may impair the control system of the flying vehicles, leading to loss of control, which could be catastrophic considering that the areas are densely populated. This thesis investigates the urban airflow characteristics that are expected to pose significant challenges to the flight of aircraft systems and impair their aerodynamic stability.