Breakwater systems play a vital role in harbor protection. Recently, breakwater deterioration has created concern regarding the durability and potential failure of the breakwater system surrounding the Chicago Harbor. The United States Engineering Research and Development Center (ERDC) created a model of the harbor and ran a series of simulations to analyze the current system and recommend to city officials any necessary improvements. However, errors were suspected during these initial simulations. This report attempts to prove/disprove the validity of their results using techniques learned in CEE 514 as well a program called STWAVE. STWAVE will model the same data used in the ERDC simulation and the hand calculations will be used to verify the accuracy of STWAVE. Finally, conclusions will be made regarding the use of STWAVE as a tool to simulate wave propagation throughout the Chicago Harbor.