Expanding pre-exposure prophylaxis (PrEP) among transgender women in the United States is an important strategy to meet national HIV prevention goals, however self-reported use of PrEP is low in this group. This study reports the findings of a cross-sectional analysis of the relationship of barriers as well as facilitators to recent PrEP use among transgender women enrolled in an evaluation of the TransLife Care project (Chicago, Illinois), a structural intervention designed to meet basic needs. We computed multivariable prevalence ratios for barriers, facilitators and recent PrEP use, controlling for demographics. Findings suggest that psychosocial and structural barriers, including moderate/high alcohol use, stimulant use, and history of incarceration were all positively associated with recent PrEP use among urban transgender women. In addition, a psychosocial facilitator, gender affirmation, was positively associated with recent PrEP use, while, while collective self-esteem, a was negatively associated with it. Finally, common indications for PrEP have high sensitivity, but low specificity and predictive value for identifying those on PrEP. We conclude that despite a large gap in PrEP use among those with indications, individuals experiencing psychosocial and structural barriers are more likely to use PrEP, and facilitators, such as psychological sense of affirmed gender may support its use. N/A.