This study reveals alternatives for Chicago’s lakefront where the city core is seamlessly connected to the lakefront. Waterfronts are important assets to a city’s economic, environmental, and social vitality. Currently, Chicago’s city core is isolated from the waterfront by a ten-lane expressway that stretches almost 16 miles parallel to Lake Michigan. Like all cities, Chicago’s earliest planners underestimated the impact the automobile would have on the urban fabric. In effect, many of these cities built super highways that severed the city from its important assets. The smartest cities have redeveloped their waterfronts which focus on pedestrian circulation, facilitate a diversity of activities, and respect the waterfront ecology. This project focused on topics including waterfront redevelopments, urban parks, and urban ecology to develop a plan to reconnect Chicago’s city core to the lakefront. An evaluation of case studies gave precedent to design, while interviews with local city leaders identified the specific needs for Chicago’s lakefront redevelopment. A thorough site analysis further identified environmental and social influences and guide design decisions toward a final plan. The master plan was based on connecting users from North and South Chicago across the Chicago River, connecting Chicago’s city core to the lakefront, promoting a diversity of recreational activities, and protecting the ecology of the lakefront.