Annually, road accidents kill thousands of children and youngsters. Road safety around the school proximity zones is a critical issue due to the high traffic volume combined with vulnerable pedestrians who cross the road. The current study aims to conduct a road safety evaluation of four different school zones located at sub-arterials and collector streets in Chandigarh city. The safety analysis and crossing risk assessment were evaluated using safety indices like the Crossing Opportunity Index and Star Rating. To identify the areas at risk, road sections in these zones were rated out of five stars using ViDa’s International Road Assessment Programme (iRAP). A star rating of ‘1’ was generated for one school and between ‘2 and 3’ for two schools under study, indicating a severe case of unsafe pedestrian crossings and high-risk zones. Headway distributions, time gap, pedestrian reaction time, and conflicting speed were used as predictors for the crossing index, which ranged between 35 and 45% for morning and evening school hours. The index suggested fewer opportunities for crossing and a lack of pedestrian-friendly infrastructure. Certain suggestive measures were proposed to increase the star rating, reduce the hazards, and make road crossing safer for children and other pedestrians.