This article traces the origins of regional planning in Chicago through the work of landscape designer Jens Jensen. It argues that the city's first regional planning efforts, led by Jensen, developed in conversation with ideas of the vernacular landscape and plant behavior at the turn of the twentieth century. Jensen's embrace of Chicago's native landscape encouraged him to adopt a regional scale of planning that celebrated urban diversity and addressed the needs of workers. His efforts, backed by the city's social reform community, spanned the successful 1904 Forest Preserve plan and the failed 1918 Greater West Park System project. Marked by contradictions, Jensen's work reveals a reform tradition distinct from the 1909 Plan of Chicago, which promoted the Forest Preserves as part of its comprehensive redevelopment program. It fused ecological metaphors with social concerns, inspiring some of the first public projects envisioned for a regional community, not an urban one.