In Latin America and the Caribbean (LAC), chikungunya (CHIK) viral infection has emerged as a significant arboviral disease. This rapidly expanding vector-borne viral illness is associated with a substantial burden of disease in terms of acute illness and also in terms of long-term sequelae. In addition, this viral pathogen has the ability to impact different populations including pregnant women and newborns. Despite the growing threat of this arboviral infection to the region, there are insufficient reports or studies attempting to delineate the clinical and epidemiological features of congenital and neonatal cases of CHIK in LAC. In this study, we present a case of congenital CHIK and a case of neonatal CHIK infection identified in Santander, Colombia. We discuss the potential neurological impact and sequelae of CHIK infection acquired during the neonatal period. There is an urgent need for further epidemiological and clinical studies to better understand the impact of CHIK in endemic areas in LAC.