The COVID-19 pandemic posed an unprecedented challenge for teachers: maintain high-quality instruction within the constraints of virtual teaching. While the difficulty of this task led to widespread teacher turnover nationally, Chicagoland teachers were more likely to remain in their schools during and after the pandemic than before it. Prior literature on teacher retention has largely focused on why teachers leave, with few studies examining those who stay, particularly in the pandemic context. This study draws on qualitative interviews with Chicagoland public school teachers to examine the varied motivations behind their decisions to persist in the profession. This study finds that men and women varied in their reasons for retention, with women emphasizing care-based motivators and men goal-oriented or external ones. This study also reports that motivations for retention varied by age and years of experience, with older, more veteran teachers focusing on challenge-oriented motivators, while younger, newer teachers emphasized external, circumstance-related motivators. This paper concludes by advocating for policies that can help mitigate gender differences and provide greater support for younger, early career teachers, as well as offering suggestions for future research.