Chesapeake sits within the Hampton Roads region with access to Virginia Beach, Norfolk, Portsmouth, Suffolk, and surrounding areas. Major highways provide regional connections, while the city's different communities offer varying levels of access to employment centers and amenities.

Chesapeake offers local restaurants, shopping, community events, historic sites, and attractions throughout the city. The Great Dismal Swamp area also provides an opportunity to explore one of the region's distinctive natural environments.

Outdoor activities are an important part of the Chesapeake lifestyle, with parks, trails, waterways, and natural areas throughout the city. Residents can enjoy hiking, cycling, fishing, boating, kayaking, and exploring the area's open spaces.