The prevalence of chronic maternal disease is rising in the last decades in the developed world. Recent evidence indicated that the incidence of chronic maternal disease ranges from 10 to 30% of pregnancies worldwide. Several epidemiological studies in mothers with chronic diseases have mainly focused on the risk for adverse obstetric outcomes. Evidence from these studies supports a correlation between maternal chronic conditions and adverse perinatal outcomes, including increased risk for preeclampsia, cesarean section, preterm birth, and admission in the Neonatal Intensive Care Unit (NICU). However, there is a knowledge gap pertaining to the management of these women during lactation. This review aimed at summarizing the available research literature regarding breastfeeding in mothers with chronic diseases. Adjusted and evidence-based support may be required to promote breastfeeding in women with chronic diseases; however, our comprehension of breastfeeding in this subpopulation is still unclear. The literature related to breastfeeding extends in various scientific areas and multidisciplinary effort is necessary to compile an overview of current evidence and knowledge regarding breastfeeding issues in mothers with chronic diseases.