This study investigated the psychological characteristics of online learning on Italian students with and without hearing loss (HL) and on their parents, who were forced into isolation during the COVID-19 pandemic. An online survey collected information on socio-demographic data and opinions concerning online learning from 61 children (mean age 11; 25 males, 36 females), including 43 with HL and also from their parents; additionally, school wellbeing and anxiety were assessed. The results showed that, in both the student and parent groups, no significant effect of HL on school wellbeing and anxiety was found. Additionally, in parents, State Anxiety was significantly higher than Trait Anxiety, suggesting one possible impact of lockdown on psychological wellbeing. Differences due to HL were observed and discussed in correlation analyses. The Authors believe that this study is the first contribution to the psychological evaluation of the impact of online learning on families with hearing-impaired children, from the perspective of a successful, inclusive didactic.