The objective of this study was to determine the most critically vulnerable major roadways in Norfolk and Virginia Beach, Virginia. Sea level rise predictions were combined with the mean higher high water and 99% tidal datums and storm surge predictions to project flood water surface elevations through the year 2100. LiDAR data were used to compare major roadway elevations to the projected flood water elevations to determine which roadway segments would be flooded under different scenarios. Traffic data were used to determine critical road segments in the region (heavily-traveled and low elevation). Results suggest that, by the year 2100, and assuming intermediate sea level predictions, nearly than 10% of major roadways will regularly flood at high tide and 15% at the 99% tide; this increases to more than 65% given a 100-year storm surge event. Five critical road segments were identified that would recurrently flood at high tide by 2100. These road segments should be the focus of infrastructure investments to improve the resiliency of the transportation network within the cities.