Since the 1860s, with the advancement of womens’ working rights, the gender wage gap has been a heavily contentious issue in U.S. political debate. While many efforts have been made to alleviate this disparity, few significant outcomes have resulted. Chicago’s recently passed Executive Order 2023:1 provides a stepping stone towards assuaging this aspect of gender parity, but it represents only a first step towards true pay equity. In this thesis, I analyze the outcomes of similar policies in two of Chicago’s sister cities to determine beneficial next steps towards womens’ workplace equality. I also include a counterfactual analysis and conduct a differences-in-differences linear regression analysis of all 50 states, followed by the same analysis for 8 select cities, to determine whether past policy initiatives have been successful or impactful on a larger scale. Following a discussion of these analyses, including testimonies from City officials, I discuss suggest policy interventions for Chicago with an emphasis on long-lasting change.