Chicago’s South Side has long been characterized as a “transit desert” – an area with high transit inaccessibility and insufficient infrastructure to meet residents’ needs (Jiao & Dillivan, 2013). Without adequate transit, residents cannot reach employment opportunities or regional amenities – contributing to economic, spatial, and social marginalization. The Chicago Transit Authority’s proposed Red Line Extension (RLE) is designed to connect the city’s far south side neighborhoods to Chicago’s core. Given the scope of the RLE, 175 parcels have been chosen for demolition, meaning that a similar number of households face displacement to make room for the RLE right of way – which may have potentially negative consequences in realizing the subsequent benefits of improved transit access. In this article, we perform an ex-ante analysis of RLE induced displacement. Specifically, we: 1) predict potential location choices that transit displacees are most likely to choose; and 2) analyze these locations in relation to access to transit, amenities, employment, and housing affordability, among others. Within the context of transportation planning, ex-ante analysis is important because it can minimize unintended and negative consequences of transit-induced displacement – like decreased transit access and a loss of potential neighborhood improvements – by predicting potential relocation choices for displacees. Such predicted choices can help planners and decision-makers better understand the trade-offs for directly affected households and thereby allow planners and decision-makers to assist in relocation assistance that maximizes the benefits of the necessarily displaced.