Cities across the globe face escalating challenges driven by rapid population growth, socio-economic disparities, underfunded infrastructure, and environmental crises, compounded by the unpredictability of modern urban dynamics. Nowhere are these issues more pronounced than in struggling urban communities, where surging costs of living—particularly for essentials like food, housing, and transportation—intensify existing inequities and jeopardize the ability of residents to sustain a decent quality of life. Traditional urban planning models often fall short in addressing these layered issues, overlooking the diverse and evolving needs of urban populations. In response to these systemic pressures, Tactical Urbanism has emerged as a promising approach. Defined by its "short-term, low-cost, and scalable interventions," it offers grassroots, community-scale solutions that resist systems prioritizing capital accumulation over communal welfare. These practices foster a collective vision of cities that celebrate shared spaces, cultural liberation, and the common good, acting as foundational steps toward addressing entrenched urban inequalities. However, as Tactical Urbanism becomes integrated into formal planning processes and increasingly intersects with privatization, concerns arise about its co-optation by neoliberal agendas, potentially diluting its transformative potential. This research critically examines the evolution of Tactical Urbanism through interviews with Chicago-based practitioners, exploring its impacts on stakeholder dynamics, its negotiation within institutional frameworks, and its role in either challenging or perpetuating existing power structures. By analyzing these developments, the study investigates Tactical Urbanism’s broader implications for urban equity, resilience, and the future of inclusive city-making.