Depending on the region and urbanization level, the rate of cycling to school in Germany varies largely. The influence of distance from home to school, educational level, the school’s region, and parents’ socio-demographic characteristics on cycling to secondary school in Germany is unclear. Therefore, this study analyzed students’ and parents’ socio-demographic correlates of cycling to school, including separate analyses by gender, among 12- to 15-year-olds attending different (sub)urban schools in Southern Germany. In 2019, 121 students (girls: 40.5%, boys: 59.5%) aged 13.1 ± 0.9 and 42 parents (mothers: 81%, fathers: 19%) aged 47.8 ± 5.5 participated. Students completed a self-report questionnaire; parents completed a self- and proxy-report questionnaire. In total, between 61.7% and 67.5% of students sometimes cycled to school. Binary logistic regressions revealed that being a girl, increasing age, attending an intermediate educational level combined with a suburban school region (small or medium-sized town), increasing distance from home to school, and having parents who did not cycle to work led to declining odds of cycling to school. Many 12- to 15-year-olds sometimes cycled to school in (sub)urban school regions in Southern Germany. As several socio-demographic characteristics correlated with cycling to school, this should be considered when developing a future school-based bicycle intervention.