While foredune geomorphology has been studied along many Great Lakes coastlines, little attention has been given to the development and evolution of foredune ridges along engineered ‘pocket’ beaches, which are common along many urban lakefronts of the region. This paper reports on the recent morphodynamics of Montrose Beach, the largest of Chicago’s engineered coastal embayments, with emphasis on its ‘Dunes Natural Area.’ A post-2020 period of beach recovery occurred after 2013–2020 lake-level rise of >1.5 m, which was accompanied by shoreline recession and overwash-induced backshore accretion. The influx of sand into the urban embayment during this time facilitated post-2020 beach recovery with lake-level fall. This phase of beach expansion was marked by the formation of three distinct, parallel berm lines that have become vegetated and functioned as focal points for eolian accretion. Undisturbed by grooming and other beach-management activities, the Dunes Natural Area continues to be influenced by lake-level changes and storms. Vegetative establishment and eolian sand trapping upon disconnect from active reworking along the shoreline have increased the expression of linear topographic highs. Seasonal ridgelines along natural beach environments, including barrier spits, tend to undergo reworking prior to such stabilization. Insights from Montrose Beach provide coastal managers with up-to-date information on important geomorphic developments at Chicago’s most popular beach destination, whose Dunes Natural Area provides habitat for the endangered Great Lakes piping plover. Understanding its geomorphic trajectory can help inform coastal resiliency planning, here and elsewhere, to protect valuable ecosystems and infrastructure within the urban coastal landscape.