Accessibility inequalities are a common trait of many Global South cities. Such inequalities are often the result of urban development trajectories and inherited practices of transport planning marked by spatial segregation and decades of car-centred development. This situation, repeated across Latin American cities, tends to affect mostly the poor in the urban peripheries. Despite available evidence of access inequalities on a case-to-case basis, comparative evidence across cities within the same region is still limited. Our paper addresses this gap by deploying a comparative accessibility assessment of inequalities in accessibility in the two Colombian cities of Bogotá and Barranquilla. Our comparison suggests that by following similar patterns of urban transport development, Bogotá and Barranquilla have reached similar accessibility and affordability patterns. Wealthier areas benefit from the triad of better transport coverage, proximity to opportunities, and higher purchasing power, while the poor in both cities face deep affordability and spatial segregation problems. Despite their similarities, our analysis reveals the effects of long-term decision-making in the number of opportunities which can be reached by different transport modes and population segments. Accessibility per capita in public transport is higher in Bogotá than in Barranquilla, and vice versa in private vehicles. These results are consistent with nearly a decade of implementation of different urban transport policies in both cities, which in Bogotá have been more public-transport-oriented than in Barranquilla. Findings also suggest that public transport-related policies can contribute to redefining urban trajectories, as both cities have experienced demographic and urban footprint increases in years. Similarities and differences in spatial and economic dimensions of accessibility serve as a mirror against which we assess transport's role in urban equality in similar global south cities. The discussion in this paper can be helpful to decision-makers as it recalls that some urban and transport policies and investments may have undesired long-term impacts in urban growth and access equality across the city.