This paper examines the disamenities associated with the Eisenhower Expressway (I-290) along the Forest Park Branch of Chicago’s Blue Line, their impacts on economic development and neighborhood connectivity within the corridor, and potential policy interventions to mitigate these challenges. Despite the corridor’s access to major employment centers, significant regional attractions, and proximity to the Loop, development outcomes have lagged compared to other transit-served areas of the city. It argues that economic development along the corridor has been constrained by the barrier effects of the expressway, which isolates the transit line from surrounding neighborhoods and limits opportunities for transit-oriented growth. Through a review of literature, analysis of corridor conditions, and assessment of public policy, the study proposes and analyses interventions to address these issues. This project contributes to broader discussions of public policy interventions that can mitigate the disamenities associated with urban freeways, with particular attention to improving economic development around the unique configuration of a rapid transit line running within a highway corridor.