Chicago’s public transit system mirrors the city’s residential segregation patterns, marginalizing communities with limited access to geographic mobility. This study expands on existing research on the spatial mismatch between workers and employment centers. I examine the improvements and renovations at the 95th/Dan Ryan Red Line terminal during the 2010s as part of Mayor Rahm Emanuel’s $8 billion investment in the CTA, aimed at addressing the spatial mismatch for low-income workers in Chicago. Through qualitative interviews with commuters and CTA staff, along with quantitative causal analysis using Census Bureau data, I find that the 95th/Dan Ryan improvements had mixed effects on the commuting experience for South Side residents. Additionally, the renovations inadvertently created a third space for criminal activity. I argue that the primarily aesthetic upgrades to the terminal are not the most effective way to stimulate economic development in historically disinvested communities. Instead, I propose policy solutions such as Red Line extensions and mixed-use zoning to more effectively revitalize the economy in Chicago’s South Side.