ObjectivesTo determine the association between individual, network, and structural COVID-19-related stressors and changes in sleep duration and quality among Black cisgender sexual minority men (SMM) and Black transgender women during the COVID-19 peak infectivity rate in Chicago. MethodsFrom April 20, 2020 to July 31, 2020, we conducted the N2 COVID Study in Chicago (n = 226). The survey included questions regarding multi-level COVID-19-related stressors (eg, food unavailability, partner violence, housing instability, concern about neighborhood COVID-19), sleep duration, and sleep quality. ResultsAbout 19.5% of our sample reported a shorter duration of sleep during the initial peak COVID-19 infectivity, while 41.2% reported more sleep and 38.9% reported about the same. Compared to the prepandemic period, 16.8% reported that their sleep quality worsened in the COVID-19 pandemic, while 27.9% reported their sleep quality had improved and 55.3% reported it was about the same. In multivariable models, we found that ≥1 day of physical stress reaction, worrying about being infected with COVID-19, traveling during COVID-19 being a financial burden, not having enough medication, knowing someone who was diagnosed with COVID-19, partner violence and housing instability were associated with poor sleep health in the COVID-19 pandemic (adjusted risk ratio: 1.82-3.90, p < .05). ConclusionsThese data suggest that COVID-19-related stressors impacted poor sleep duration and quality during the pandemic among this cohort. Multi-level interventions to reduce COVID-19-related stressors (eg, meditation, intimate partner violence prevention and housing programs) may be useful for improving sleep health among Black cisgender sexual minority men and Black transgender women.