Urban climate knowledge has been increasingly integrated into urban design and planning practices. Numerical modeling systems, such as climatic and bioclimatic tools, are currently more popular than onsite field measurements. This higher popularity is mainly due to the complicated interactions in 3D urban environments and the spatial distribution of various climatic parameters that cannot be captured thoroughly via on-site measurements alone. Such modeling systems also offer better solutions to overcome the nonlinearity of urban climate in forecasting different "what if scenarios." This paper provides an overview of different types of climatic and bioclimatic modeling systems and presents their main benefits and shortcomings. In the second part of this study, one of the most commonly used tools in urban climate studies, namely, ENVI-met, was selected, and its reliability in different contexts was investigated by reviewing past researches. The applicability of ENVI-met in accurately simulating the influence of future urban growth on one of the fastest growing suburbs in Melbourne, was tested by conducting a sensitivity analysis on inputs and control parameters, backed up with a series of field measurements in selected points. RMSE value was calculated for different runs of the initial ENVI-met model with adjusted control parameters (e.g., factor of short-wave adjustment, initial air temperature, relative humidity, roughness length, wind speed, albedo of walls, and albedo of roofs). The model achieved the optimum performance by altering the short-wave adjustment factor from 0.5 to 1; therefore, ENVI-met was considered a reliable tool for relative comparison of urban dynamics. The findings of this study not only help planners select the most practical modeling systems that address project objectives but also educate them on limitations associated with using ENVI-met.