While many major cities in the United States are once again gaining population, growing their economies, and attracting talent, many small and mid-sized cities are in decline. The reasons for this growing disparity are multi-faceted. A growing body of research has been exploring planning challenges in declining cities and towns. This body of research—often called “shrinking cities” and “urban shrinkage” research—is premised on the belief that many declining places will continue to shed population, jobs, and industries, and planning smartly for this decline is the only sensible path forward. So far, research in the U.S. has focused primarily on Northeast and Midwest cities where population and industrial decline has been the most severe. Less scholarship has studied places that have declined more slowly and more recently. This thesis examines the current trends impacting the decline of mid-sized cities in the Midwestern United States, focusing on four cities in the State of Illinois. It also explores whether these cities are ready to consider the possibility that population decline is not temporary and change their planning strategies accordingly. Finally, this thesis will introduce an emerging paradigm in contemporary urban planning practice that fuses growth and decline strategies, to prepare mid-sized cities for an uncertain demographic and economic future.