Background: Families in high-risk communities for COVID-19 transmission experienced a disproportionate burden during the pandemic. This study assessed these families' needs, changes in children's well-being, and perceptions related to the pandemic. Methods: Four online surveys were administered January 2021 to September 2021 to parents of students, enrolled in parochial, kindergarten-eighth grade schools in Chicago neighborhoods with higher COVID-19 incidence rates by ZIP code, compared to the city average, and higher resource need. Results: The response rate was 69.1% (n = 186 of 269) in the baseline survey; and other surveys were at 1 (n = 151), 3 (n = 145), and 5 months (n = 154). Of the sample, 83% of parents identified as Hispanic/Latinx with a mean age of 38.3 years (SD: 8.5). Approximately a quarter of parents reported difficulty paying cable and internet bills (26%) and paying utilities (25%). Parents reported children as happy (94% and 95%, p = 0.59) and hopeful (96% and 95%, p = 0.74) at 1-month (February to May 2021) and 5-month surveys (June to September 2021). Parents also reported fewer children were irritable (29% vs 19%, p = 0.03), felt lonely (17% vs 10%, p = 0.03), and felt isolated (28% vs 9%, p < 0.001) between those survey waves. The majority (67%) of parents felt that their child had no difficulty wearing a mask in public. Conclusions: In this longitudinal study, Chicago parents rated children's well-being highly and reported a decrease in negative emotions over time. The areas of need identified may be particularly relevant for outreach and providing resources to Hispanic/Latino families in future emergencies or global health threats.