Urban expressways have long been scrutinized for their destructive impacts on the built environment, public health, and the planet. However, the specific impact of Chicago’s DuSable Lake Shore Drive on the livability of nearby neighborhoods has yet to see substantial academic scrutiny. To fill this gap, this research seeks to understand (1) if a neighborhood’s livability changes depending on proximity to the expressway and (2) if the expressway’s wall-like structure and high-speed traffic stifle livability by interrupting pedestrian access to lakefront parkland. Livability variables derived from a New Urbanist framework—Population Density, Walk Score, Bike Score, and Transit Score—were used for the analysis. Geographic Information Science was used to examine each variable’s spatial relationship to the expressway in three study areas and to visualize gaps in convenient pedestrian access to the lakefront parks across the expressway via official crosswalks, bridges, and tunnels. Results show: (1) Population density appears to decrease with lakefront distance within every study area while transit access appears to increase, but more advanced methodology is required to determine correlation. (2) Walkability and bikeability have inconsistent relationships with lakefront distance across study areas. (3) Walkability, bikeability, and transit access rapidly increase when moving inland up to 0.2 miles from the lakefront. (4) There are large gaps in pedestrian access to lakefront parks across the expressway which are disproportionately located within historically disinvested neighborhoods on Chicago’s South Side. From these findings, the urban design tool Streetmix was used to produce a vision proposal for a more equitable and livable waterfront through a Boulevardization approach designed to promote multimodality and population density.