Increased urban development in American cities has led to higher stormwater runoff quantities entering local sewer systems and combined sewer overflows (CSOs) during strong storm events. The task of preventing CSOs has traditionally been met by unsustainable grey ‘end-of-pipe’ solutions, which aim to increase the capacity of local sewer systems to handle the additional stormwater runoff. However, these practices fail to recognize the underlying issue: increased runoff from impervious developments. Therefore, a transition to green infrastructure (GI) is necessary to ensure sustainable stormwater management by decreasing impervious surface areas in the effort to simulate pre-development environments and runoff quantities. This dissertation aims to assist in this transition by giving engineers the tools to develop and evaluate GI plans tailored to the needs of their city, through a multi-criteria decision analysis (MCDA) and cost-benefit analysis (CBA) framework and database spreadsheet calculator. This tool is utilized for the recommendation of a GI plan for Lincoln Park, Chicago, along with a plan for successful implementation. Serving as a model for other cities to follow, this analysis shows the strategy needed for a shift to sustainable stormwater management.