Due to complicated building geometries and heterogeneous urban morphologies, project-specific wind analysis is needed in addition to the general understandings of wind environment in order to develop appropriate mitigation strategies for any particular projects that may have outdoor natural ventilation issues. Over the past few decades, rapid development in computational fluid dynamics (CFD) has resulted in itself widespread application in environmental research and design. This chapter introduces a systematic wind analysis to accurately model wind environment and efficiently analyze modeling results to support evidence-based decision-making during design procedure. By conducting a case study in Hong Kong, this chapter addresses issues from input boundary condition setting, modeling settings, modeling verification, to data collection and analysis, which may be encountered by wind consultants and architects when conducting wind analysis. Various statistical analysis methods are applied to compare simulation results, diagnose the designs, and develop corresponding mitigation strategies in terms of natural ventilation performance.