For African American (AA) families on Chicagoland's South Side who choose to breastfeed, finding and receiving services needed to reach their goals are difficult. The disparities in breastfeeding support across Chicagoland are symptomatic of inequitable health care access shaped by persisting structural racism. A number of community hospitals that once served AA families by providing easy access to care no longer exist. Recently, South Side obstetric unit and hospital closures have increased. Simultaneously, funding is increasingly competitive for community health organizations and federally qualified health centers. Institutions and agencies that do receive funding or adequately allocate funding to include lactation services cannot address breastfeeding barriers within socioeconomically marginalized communities. The unmet funding needs not only affect breastfeeding families but also impede the growth of a multilevel lactation care workforce. Finally, inconsistencies persist between breastfeeding information provided by lactation providers and delivery team care received in the hospital. Despite these barriers, we believe pathways exist to improve breastfeeding rates among South Side AA communities, such as perinatal home visiting services. Stakeholders must recognize the longstanding effects of structural racism and address the inequitable distribution of perinatal care across Chicagoland. Stakeholders must also place value in and be supportive of lactation care providers and the families they serve through both funding and policies. These changes, in addition to community-level collaboration, can improve breastfeeding rates for AA families on Chicagoland's South Side.