In 2020, school closure due to the COVID-19 pandemic necessitated the increased usage of technology to allow students to continue their education in a distant learning environment, raising further attention to digital inequality and its consequences on students’ educational experiences and outcomes. Due to the lack of digital access or other unfavorable circumstances, non-digital learners – students who were not able to engage in remote learning at the beginning of the abrupt school closure – in Chicago Public Schools (CPS) used paper-based learning materials during Spring 2020, instead of learning online like their peers did. To address the digital divide, the Chicago Connected (CC) program has provided free high-speed Internet connection to eligible CPS students since June, 2020. Using CPS administrative data, this study examined the take up and effectiveness of CC among non-digital learners. While black students and students experiencing higher levels of economic hardship were overrepresented among non-digital learners, Hispanic, LEP, and homeless students among them were more likely to take up CC. Using multiple statistical models, this study also found that taking up CC had insignificant impacts on attendance and grades in the fall semester following its implementation after controlling for student characteristics and performance during Spring 2020. Potential reasons for null effects were discussed, and the results may indicate that researchers, policymakers, and practitioners need to understand the underlying social problems beyond the physical digital divide, and strategies targeting the needs of non-digital learners should be integrated to address the gaps in learning outcomes.