Empirical research on parents’ decision making process and parents’ actual criteria when considering preschool is critical when considering its relationship to early educational experiences and subsequent outcomes for children. Research has consistently demonstrated that the type and quality of preschool program children attend has implications for future academic success. A review of past research suggests parents often have difficulty assessing quality and include a wide range of considerations that include both practical and educational features of care. The current study utilized a transactional ecological framework to examine parent considerations and related family, child and cultural factors. A series of focus groups and interviews were conducted with parents to identify parent considerations and inform creation of a survey measure designed to assess these considerations. Surveys were then completed by 203 parents from varying socioeconomic and ethnic backgrounds who had a child that qualified for state-funded preschool the following year. Parents were recruited from 20 centers including Head Start programs, private-for profit programs, religiously affiliated programs and one YMCA center. Exploratory factor analysis identified two highly correlated categories of considerations: 1) characteristics that designate several types of quality indicators and 2) characteristics that designate a program’s practical features. A series of hierarchical regressions indicated a combination of cultural, family and child factors are important when assessing parents’ considerations for pre-kindergarten. In particular, socioeconomic status, parents’ beliefs about childrearing and involvement and children’s prosocial skills and family structure were uniquely related to parental endorsement of quality and practical considerations. These findings have important implications for policymakers and practitioners