Listening difficulties may frequently occur in school settings, but so far there were no tools to identify them for both hearing and hearing-impaired Italian students. This study performed cross-cultural adaptation and validation of the Listening Inventory for Education-Revised for Italian students (LIFE-R-ITA). The study procedure followed the stages suggested by the Guidelines for the Process of Cross-cultural Adaptation of Self-Report Measures. For the content validation, six cochlear implanted students (8-18 years old) pre-tested the initial version. Whenever any situation did not occur in Italy, the item was adapted to more typical listening situations in Italy. The final version of LIFE-R-ITA was administered to a sample of 223 hearing students from different school settings and educational degrees in order to collect normative data. For the LIFE-R-ITA, hearing students showed an average score of 72.26% (SD = 11.93), reflecting some listening difficulties. The subscales (LIFE total, LIFE class, and LIFE social) indicated good internal consistency. All items were shown to be relevant. Most challenging situations happened when listening in large rooms, especially when other students made noise. LIFE social scores were significantly worse than those of LIFE class (p < 0.001). The present study provides cross-cultural adaptation and validation for the LIFE-R-ITA along with the normative data useful to interpret the results of students with hearing loss. The LIFE-R-ITA may support teachers and clinicians in assessing students' self-perception of listening at school. Such understanding may help students overcome their listening difficulties, by planning and selecting the most effective strategies among classroom interventions.