We determined which variables are predictive of normal-weight (N) Chilean 4-year-olds developing overweight/obesity when entering primary school. This study used national data of preschoolers (PK, age 4) in 2011 through 2015, and the same children in the first grade (1st G, age 6) in 2013 through 2017. We formed longitudinal cohorts considering PK as the baseline and 1st G as the follow-up and included anthropometric, socio-demographic, and health variables in PK and anthropometry in the 1st G. We report the percentage N who remained N at follow-up (N-N) or gained excessive weight (N-OW) and (N-OB), by sex. We ran univariate logistic regressions to determine for each variable, its association with gaining excessive weight (N-OW + OB), incorporating significant variables (p < 0.001) in multivariate logistic regression. A total of 483,509 (251,150 girls) of PK had anthropometry in the 1st G. In PK, 22% of the children were obese; in the 1st G (24.8% and 19.7% in boys and girls, respectively). Of normal-weight children, 30% developed OW + OB. The predictive variables were: Being born macrosomic, attending a very vulnerable school, being indigenous, the mother’s low schooling, and the child being cared for by the grandmother after school. In this study, the factors predicting that normal-weight preschoolers gain excessive weight gain in a short period of time are mostly related to poverty. Prevention should focus on this population.