In order to deal with the complicated turbulence issues, a variety of turbulence models are built in the Computer Fluid Dynamic (CFD) software. Large Eddy Simulation (LES) is a time dependent calculation which is superior to direct numerical simulation in computing time and cost, and more information and more accurate results can be obtained by LES model than any other traditional methods. Based on the LES model, this paper makes a comprehensive analysis on the pressure distribution of a typical cuboid building, Commonwealth Advisory Aeronautical Council (CAARC), using CFD software with the Shanghai meteorological data in the latest few years. First, numerical results are obtained when the building is on the windward side in this work which is used to check the correctness of the model compared with the wind tunnel measurements and then simulations in other wind directions are completed. As a result, the pressure and the stress of the building’s surface in different wind directions are obtained and then it can be used to provide reference for city construction.