Walking and biking to school represent a source of regular daily physical activity (PA). The objectives of this paper are to determine the associations of distance to school, crime safety, and socioeconomic variables with active school transport (AST) among children from five culturally and socioeconomically different country sites and to describe the main policies related to AST in those country sites. The analytical sample included 2845 children aged 9–11 years from the International Study of Childhood Obesity, Lifestyle and the Environment. Multilevel generalized linear mixed models were used to estimate the associations between distance, safety and socioeconomic variables, and the odds of engaging in AST. Greater distance to school and vehicle ownership were associated with a lower likelihood of engaging in AST in sites in upper-middle- and high-income countries. Crime perception was negatively associated to AST only in sites in high-income countries. Our results suggest that distance to school is a consistent correlate of AST in different contexts. Our findings regarding crime perception support a need vs. choice framework, indicating that AST may be the only commuting choice for many children from the study sites in upper-middle-income countries, despite the high perception of crime.