This essay examines the implications of rapid technological and economic change, or what economist Joseph Schumpeter called “creative destruction,” for the urban environment. Taking the Chicago River Harbor as a case study, it argues that industrial capitalism was marked by fundamental spatial and environmental contradictions that resulted in the frequent destruction and reinvention of urban landscapes. The essay shows how transformations in the Great Lakes shipping industry and the rise of the steel industry rendered Chicago River Harbor infrastructure obsolete. That obsolescence, in turn, sparked a public debate over whether the port should be retrofitted or if the river should be harnessed for different uses. So many stakeholders—streetcar companies, commuters, City Beautiful advocates, and sanitary engineers—had conflicting ideas about the use of the river that it was practically impossible to retrofit the port. The resulting decline of industrial freight traffic on the Chicago River enabled urban planner Daniel Burnham to reinvent the riverfront as a site of leisure and consumption.