The Sub-Andean retroarc region is a unique example of an active continental-scale retroarc foreland basin system. Heavily targeted for hydrocarbon exploration, the region hosts a large volume of subsurface data coupled to surface studies dedicated to refining its evolution in time and space. This paper presents a regional correlation of stratigraphic markers from seismic reflection and well logs across the Sub-Andean foothills at 23−21°S in southern Bolivia and northern Argentina, which reveals the contrasting along-strike history of Mesozoic to Cenozoic tectonics that preceded the foreland basin setting. Supported by published geochronological data and new zircon U-Pb maximum depositional ages, we describe the depositional transition from pre-Andean to Andean stratigraphy and discrete episodes of foreland basin subsidence and shortening. Based on interpreted stratigraphic breaks, we define the extent and stepwise evolution of this foreland basin, which was characterized by the progressive eastward migration of foreland basin depozones. Based on restored thickness profiles, we present flexural models of basin subsidence for the Sub-Andean foothills region. The modeling of discrete episodes of foreland basin subsidence refines the widely accepted bimodal elastic strength in the foreland basin at 21−23°S, which is weaker in the western ranges (∼20 km effective elastic thickness) and stronger eastward (>40 km). Modeling results also reveal minimum values of subsidence rates (up to 1.2 mm/yr) in the sequential foredeep depozones and suggest that the modeled tectonic load migration—as constrained by the record of syntectonic strata—probably increased over time through the incorporation of Sub-Andean rocks into the orogenic wedge.