Nearly all schools in the United States closed in spring 2020, at the onset of the COVID-19 pandemic. With a micropolitical lens, we analyze traditional public and charter schools reopenings for the 2020-21 school year in five urban districts. Districts’ adherence to and strategic uses of public health guidance, as well as a combination of union-district relations and labor market dynamics, influenced reopening. Parents, city and state lawmakers, and local institutional conditions also played a role, helping to explain differences across cases. We provide a rich description of reopening decisions in each of our case districts, and offer theoretically-grounded explanations for how factors identified in prior studies—which were interrelated and varied across local contexts—influenced district decision-making.