Comprehensive citywide planning is a practice that many cities undertake regularly. In theory, the principles laid out in citywide plans can help guide the distribution of public and private investments that shape the future development of that city. In recent years, many major cities have been incorporating equity goals and frameworks into planning efforts in attempts to close long-standing racial gaps. Although urban planning, as a field, has espoused goals of participation and shared power in development decisions, power and influence is often concentrated among wealthier households and institutions. Participation in planning processes often involves conflict between opposing interests, and development outcomes are often inequitable. Comprehensive planning has the potential to change some development rules and processes that lead to inequitable outcomes, but this is contingent upon shifting power and influence away from wealthy and elite citizens and institutions. Research on power and empowerment is critical to understanding how influence is manifested through planning policies and processes. The City of Chicago’s “We Will Chicago” plan provides a case example of how city planning processes attempt to engage stakeholders in developing a vision and goals that align with traditionally marginalized groups.