Toll Road

Toll Road

Tolls in Chesapeake are currently limited to the Chesapeake Expressway, but new ones may be imposed on some existing facilities to help generate revenue for transportation projects in the region.

Airports

Chesapeake is served by the nearby Norfolk International Airport in the City of Norfolk with commercial airline passenger service.
Within the city limits, Chesapeake Regional Airport is a general aviation facility located just south of Great Bridge. Also within the city, is the Hampton Roads Executive Airport located near Bowers Hill and the Hampton Roads Beltway. This airport caters to private airplane owners and enthusiasts. South of there, NALF Fentress is facility of the U.S. Navy and is an auxiliary landing field which is part of the large facility at NAS Oceana in neighboring Virginia Beach.

River and Ports

The Intracoastal Waterway passes through Chesapeake. Chesapeake also has extensive frontage and port facilities on the navigable portions of the Western and Southern Branches of the Elizabeth River.
The Dismal Swamp Canal runs through Chesapeake as well. The site of this canal was surveyed by George Washington, among others, and is known as "Washington's Ditch". It is the oldest continuously used man made canal in the United States today and has been in service for over 230 years. The canal begins in the Deep Creek section of the city branching off from the Southern Branch of the Elizabeth River. The canal runs through Chesapeake paralleling U.S. Highway 17 into North Carolina and connects to Elizabeth City, North Carolina.

Rail

Five railroads currently pass through portions of Chesapeake, and handle some intermodal traffic at port facilities on Hampton Roads and navigable portions of several of its tributary rivers. The two major Class 1 railroads are CSX Transportation and Norfolk Southern, joined by three short line railroads.
Chesapeake is located on a potential line for high speed passenger rail service between Richmond and South Hampton Roads which is being studied by the Virginia Department of Rail and Public Transportation. A new suburban passenger station near Bowers Hill would potentially be included to supplement a terminal in downtown Norfolk.

Highways

• I‑64 / I‑464 / I‑664 / US 13 / US 17 / US 58 / US 460 / SR 168
• Future I‑87

Chesapeake is served by U.S. Highways 13, 17, 58, and 460. Interstate 64, part of the Hampton Roads Beltway, crosses through the city, Interstate 464 is a spur which connects it with downtown Norfolk and Portsmouth at the Berkley Bridge, and Interstate 664, which completes the Interstate loop from the Western Branch section of Chesapeake through the city of Newport News and into the city of Hampton.
State Route 168 is also a major highway in the area. It includes the Chesapeake Expressway toll road.
Chesapeake is the only locality in the Hampton Roads area with a separate bridge division. The city's Department of Public Works, Bridges and Structures division has 51 full-time workers. The city maintains 90 bridges and overpasses. Included are five movable span (draw) bridges which open an estimated 30,000 times a year for water vessels.^[21]
North Carolina and Virginia have been looking to connect Raleigh, North Carolina and the Hampton Roads area. In mid-2016, AASHTO and the FHWA approved Interstate 87 for the route. Originally, Interstate 89 was proposed for the route if an north-south designation was chosen, and Interstate 44 if an east-west designation was chosen. These two proposed designations would not have been continuous with Interstate 89 in New Hampshire and Vermont, and Interstate 44 in Texas, Oklahoma, and Missouri.