In the past two centuries, many American urban areas have experienced significant expansion in both populating and depopulating cities. The pursuit of bigger, faster, and more growth-oriented planning parallels a situation where municipal decline has also been recognized as a global epidemic. In recent decades many older industrial cities have experienced significant depopulation, job loss, economic decline, and massive increases in vacant and abandoned properties due primarily to losses in industry and relocating populations. Despite continuous economic decline and depopulation, many of these so-called shrinking cities still chase growth-oriented planning policies, due partially to inabilities to accurately predict future urban growth/decline patterns. This capability is critical to understanding land use alternation patterns and predicting future possible scenarios for the development of more proactive land use policies dealing with urban decline and regeneration. In this research, the city of Chicago, Illinois, USA is used as a case site to test an urban land use change model that predicts urban decline in a shrinking city, using vacant land as a proxy. Our approach employs the Land Transformation Model (LTM), which combines Geographic Information Systems and artificial neural networks to forecast land use change. Results indicate that the LTM is a good resource to simulate urban vacant land changes. Mobility and housing market conditions seem to be the primary variables contributing to decline.