The purpose of this research was to evaluate the level of school connectedness and feelings about school among Icelandic preteenagers who were either with or without a chronic health condition. The study is cross-sectional with 480 children of 10–12 years old (209 boys and 271 girls) and 38 teachers participating from 12 randomly selected public elementary schools in Reykjavik, Iceland. Data were collected from March 2004 to early June 2004. Independent t-tests and multivariate regression analyses were used to test the hypotheses. Girls were found to report significantly higher connectedness to their school and significantly higher positive feelings about their school than the boys. Children with chronic illnesses were found to report significantly lower school connectedness and significantly lower positive feelings about their school than children without chronic illness(es). Further, Icelandic preteenagers with a mental illness or learning disabilities were found to report significantly lower school connectedness and significantly lower positive feelings about their school than their school mates who had physical chronic illness(es). The teachers’ perception of children’s social competence significantly predicted both the girls’ and the boys’ perception of their connectedness to school and feelings about school. Preventive actions need to be taken by school nurses and other school personnel to prevent disengagement in schools, especially for preteenage boys and for chronically ill children, specifically children dealing with mental illnesses or learning disabilities.