Chesapeake, Virginia, located about 20 miles inland from the Atlantic Coast, is no stranger to the threats posed by hurricanes and severe coastal storms. Due to its relative proximity to the coast and low elevation, the city is especially prone to flooding. More specifically, Southern Chesapeake is mostly flat and low-lying, and it borders the Great Dismal Swamp, making it prone to severe flooding during heavy rainfall events associated with tropical cyclones. Historically, Chesapeake has weathered several significant storms. For instance, in 2003, Hurricane Isabel caused extensive damage in the area, especially from floodwaters. It remains one of the costliest and deadliest hurricanes in Virginia's history. More recently, in 2011, Hurricane Irene resulted in significant flooding and wind damage in Chesapeake. Also, Hurricane Matthew in 2016 resulted in widespread flooding in the city. Therefore, in considering potential hurricane threats for Chesapeake, both historic flooding and wind damage should be taken into account. Special consideration should be given to boosting community preparedness and infrastructure resilience, especially in the flood-prone southern region of the city.