How far is South Boston, VA from Chesapeake, VA?
The driving distance from South Boston, VA to Chesapeake, VA is about 164 miles (264 km), with a travel time of about 02h 54m by car.
- The straight-line flight distance is about 145.6 miles (234.4 km).
- For a round trip, plan for roughly 05h 48m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 8:00 AM to 10:00 AM EDT.
Reverse, save, or send this route
This route works well as a day trip with time at the destination. Copy the route link, send it to another device, or print a clean version before you head out.
This route works well as a day trip with time at the destination.
Flight Distance
Driving Distance
Gas Cost Calculator
Leave and Arrive Planner
Pick a departure time to see your estimated arrival and same-day return window.
Drive time stays fixed at 02h 54m.
A morning start gives you useful time at the destination and keeps the return out of the late evening.
You are leaving earlier than the recommended window, which gives you extra margin for breaks and traffic.
Halfway Point
A useful midpoint for breaks, coffee, or meeting in the middle.
Independent city in Virginia, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Chance Rain Showers
Rain Showers Likely
Driving Route Map
The map below follows the saved road route between South Boston and Chesapeake.
Turn-by-Turn Driving Directions
Step-by-step road directions between South Boston and Chesapeake.
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1
Start on North Main Street
28 m · 5 sec · North Main Street
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2
Continue on Main Street
931 ft · 40 sec · Main Street
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3
Turn left onto Seymour Drive
1.1 km · 1 min · Seymour Drive
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4
Turn right onto James D Hagood Highway
964 ft · 20 sec · James D Hagood Highway
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5
Continue on John Randolph Boulevard
2202 ft · 44 sec · John Randolph Boulevard
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6
Turn left onto Bill Tuck Highway
18.1 mi · 23 min · Bill Tuck Highway
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7
Continue on Clarksville Bypass
3.6 mi · 5 min · Clarksville Bypass
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8
Keep slight right to continue on Clarksville Bypass
19.2 mi · 25 min · Clarksville Bypass
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9
Continue on Highway 1
3.5 mi · 5 min · Highway 1
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10
Continue on South Hill Bypass
3.3 mi · 5 min · South Hill Bypass
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11
Continue on East Atlantic Street
1.1 mi · 2 min · East Atlantic Street
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12
Continue on Highway 58
3.6 mi · 5 min · Highway 58
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13
Continue on Piney Pond Road
1.2 mi · 2 min · Piney Pond Road
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14
Continue on Governor Harrison Parkway
22.5 mi · 30 min · Governor Harrison Parkway
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15
Continue on Pleasant Shade Drive
6.4 mi · 9 min · Pleasant Shade Drive
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16
Continue on West Atlantic Street
5.1 mi · 7 min · West Atlantic Street
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17
Continue on Southampton Parkway
62.1 mi · 1 hr 21 min · Southampton Parkway
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18
Continue on West Military Highway
1.7 mi · 2 min · West Military Highway
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19
Take the exit slight right toward I 264 East, I 64, US 13 North: Portsmouth, Norfolk, Va Beach
1.2 km · 2 min
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20
Keep slight left to continue on I 264 East, I 64, US 13 North: Portsmouth, Norfolk, Va Beach
2322 ft · 57 sec
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21
Merge slight left onto Hampton Roads Beltway
3026 ft · 43 sec · Hampton Roads Beltway
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22
Take the exit slight left toward I 264 East: Portsmouth, Norfolk
1.2 km · 1 min
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23
Continue straight
3.7 mi · 5 min
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24
Take the exit slight right toward VA 164 West, US 17: Martin Luther King Jr Expressway, Norfolk, Frederick Boulevard
920 ft · 23 sec
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25
Keep slight right to continue on US 17: Frederick Boulevard
1070 ft · 28 sec
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26
Turn right onto Frederick Boulevard
1.2 mi · 2 min · Frederick Boulevard
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27
At the end of the road, turn left onto George Washington Highway
1964 ft · 50 sec · George Washington Highway
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28
Turn right onto Elm Avenue
1.3 km · 1 min · Elm Avenue
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29
Continue on South Norfolk Jordan Bridge
1.1 mi · 2 min · South Norfolk Jordan Bridge
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30
Turn straight onto Poindexter Street
1.1 km · 1 min · Poindexter Street
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31
Turn left onto D Street
126 m · 18 sec · D Street
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32
Arrive at your destination
0 m · 1 sec · D Street
Car Route Details
A richer read on the saved driving route between South Boston and Chesapeake.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
Southampton Parkway
Continue on Southampton Parkway
62.1 mi · 01h 21m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A comfortable day-trip route
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
Chance Rain Showers leaving South Boston and Rain Showers Likely near Chesapeake.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from South Boston to Chesapeake?
The road trip is about 164 miles (264 km) and usually takes 02h 54m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
What is the halfway point on this route?
Emporia is a useful midpoint, sitting about 81.7 miles from South Boston and 82.3 miles from Chesapeake.
How much longer is the road route than the straight-line distance?
The direct path is about 145.6 miles (234.4 km), while the road route adds roughly 18.4 extra miles because roads do not follow the straight air line.
When is the best time to leave for this route?
A good departure window is usually 8:00 AM to 10:00 AM EDT. If you want a more comfortable same-day return, try to leave by 12:42 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $22.93 one way or $45.87 round trip. Estimated CO2 is about 51.5 kg one way.
What should you check before leaving?
Before you leave, expect Chance Rain Showers around South Boston and Rain Showers Likely near Chesapeake.
Stop Ideas Near Emporia
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Emporia.
Petersburg station
Rocky Mount
Richmond Main Street Station
Williamsburg Transportation Center
Flight Path Map
This map shows the direct air route between South Boston and Chesapeake. Straight-line distance: 145.62 mi (234.35 km).
#1 South Boston
Town in Halifax County, Virginia, United States
| Population | 7,519 |
| Coordinates | 36.6987500, -78.9014000 |
| Altitude | 131 |
| Country | United States |
#2 Chesapeake
The second most populous city in Virginia.
| Population | 247,011 |
| Coordinates | 36.8190400, -76.2749400 |
| Altitude | 3 |
| Country | United States |
End: D Street (-76.275044, 36.81897)
Estimated Travel Time
Distance: 264 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 05h 27m |
| 40 mph (64.37 km/h) | 04h 06m |
| 50 mph (80.47 km/h) | 03h 16m |
| 60 mph (96.56 km/h) | 02h 44m |
| 70 mph (112.65 km/h) | 02h 20m |
| 80 mph (129 km/h) | 02h 02m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.96 | $22.93 | $45.87 |
| Mid-grade | $4.43 | $25.64 | $51.29 |
| Premium | $4.78 | $27.66 | $55.33 |
| Diesel | $5.62 | $32.56 | $65.13 |
Assumes 8.3 L/100 km (about 28.3 MPG). CO2 is an estimate and varies by vehicle, fuel blend, traffic, and terrain.
Prices in Virginia · Apr 19, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.