The presence of obstacles in the propagation path is a critical factor in air-to-ground (AG) communication. The behavior of wireless signal propagation depends on several variables, such as frequency, building height, elevation angle, and street design. This paper aims to compare the three established line of sight (LOS) probability model based on actual site data, including the building geometry in suburban environment. The comparison between these three models using the site data provide a guideline for selecting the LOS probability model based on the optimistic and pessimistic predictions. The shadowing loss was evaluated at frequencies 2 and 3.5 GHz with an elevation angle of 20° in two suburban locations at Universiti Tun Hussein Onn Malaysia. Three prediction models, ITU-R P.1410-5, Holis and Pechac, and Pang et al., available in the literature were used to identify and compare the line-of-sight probability. By focusing on the shadowing model in suburban area, the guideline for optimizing LOS communications or navigation in these challenging environments can be developed. The finding highlights the importance of considering building height in AG communication for network performance evaluation and design.