Parental expectations could be considered as the best indicator of parental involvement for a child's educational success. They are mainly explained by the characteristics of students and their families. Recent researches encourage a better consideration of the school or country characteristics. Our study was carried out in Chile, a country with high school segregation. The objective was to test a multi-level model explaining parental Chilean expectations integrating individual, familial and school factors. We used a semi-longitudinal design, and our study sample (N= 95,045 Chilean students) came from a national assessment that was conducted in 2015 and 2017, when students were in their 8th and 10th grades. Our results showed that while individual characteristics and family context were linked to the development of parental expectations, the school environment also has a role to play in their construction. In Chile, the parents with lower socio-economic resources send their children to more disadvantaged schools. Children with low family socio-economic resources are doubly penalized: their parents had low expectations due to their socio-economic level and due to the school they can send their children.