How far is Chesapeake, VA from South Boston, VA?
The driving distance from Chesapeake, VA to South Boston, VA is about 164.6 miles (264.9 km), with a travel time of about 03h 41m by car.
- The straight-line flight distance is about 145.6 miles (234.4 km).
- For a round trip, plan for roughly 07h 23m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 8:00 AM EDT.
Reverse, save, or send this route
This drive is better planned with a longer stop or an overnight stay. Copy the route link, send it to another device, or print a clean version before you head out.
This drive is better planned with a longer stop or an overnight stay.
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 03h 41m.
An early departure helps you fit a real stop into the day without turning the return into a late-night drive.
This departure sits inside the recommended comfort window for the route.
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.
Rain Showers Likely
Chance Rain Showers
Driving Route Map
The map below follows the saved road route between Chesapeake and South Boston.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chesapeake and South Boston.
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1
Start on D Street
126 m · 21 sec · D Street
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2
At the end of the road, turn right onto Poindexter Street
1617 ft · 29 sec · Poindexter Street
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3
Take the ramp straight toward I 464 North
1284 ft · 18 sec
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4
Merge slight left
1.2 mi · 1 min
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5
Keep slight right to continue on I 264 West Toll: Downtown Tunnel, Portsmouth
580 ft · 14 sec
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6
Keep slight left to continue on I 264 West Toll: Tunnel
2569 ft · 1 min
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7
Merge slight left
6.7 mi · 10 min
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8
Keep slight right to continue on I 664: Bowers Hill, Suffolk, Richmond
1 km · 47 sec
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9
Merge slight left onto Hampton Roads Beltway
2197 ft · 31 sec · Hampton Roads Beltway
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10
Take the exit slight right toward US 13, US 58, US 460, VA 191 North: Suffolk, Military Highway
1598 ft · 54 sec
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11
Keep slight left
3155 ft · 1 min
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12
Continue on West Military Highway
2.4 mi · 3 min · West Military Highway
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13
Continue on Portsmouth Boulevard
62.1 mi · 1 hr 21 min · Portsmouth Boulevard
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14
Continue on Courtland Road
5.2 mi · 7 min · Courtland Road
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15
Continue on Pleasant Shade Drive
6.3 mi · 9 min · Pleasant Shade Drive
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16
Continue on Governor Harrison Parkway
22.5 mi · 30 min · Governor Harrison Parkway
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17
Continue on Piney Pond Road
1.2 mi · 2 min · Piney Pond Road
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18
Continue on Highway 58
3.5 mi · 5 min · Highway 58
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19
Continue on East Atlantic Street
1.1 mi · 2 min · East Atlantic Street
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20
Continue on South Hill Bypass
3.5 mi · 5 min · South Hill Bypass
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21
Continue on Highway 1
3.2 mi · 4 min · Highway 1
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22
Continue on Highway 58
18.9 mi · 24 min · Highway 58
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23
Turn straight onto Clarksville Bypass
4 mi · 5 min · Clarksville Bypass
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24
Continue on Highway 58
18 mi · 23 min · Highway 58
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25
Turn right onto John Randolph Boulevard
1 km · 1 min · John Randolph Boulevard
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26
Turn left onto Seymour Drive
1.1 km · 1 min · Seymour Drive
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27
Turn right onto Broad Street
1158 ft · 49 sec · Broad Street
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28
Turn left onto North Main Street
124 m · 8 sec · North Main Street
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29
Arrive at your destination
0 m · 1 sec · North Main Street
Car Route Details
A richer read on the saved driving route between Chesapeake and South Boston.
Interchange-aware route
The drive includes several ramps, exits, or merges, so checking the next few maneuvers before busy interchanges is useful.
Portsmouth Boulevard
Continue on Portsmouth Boulevard
62.1 mi · 01h 21m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A longer out-and-back drive
This is still possible in one day, but it becomes a long driving day. Leaving early and planning your stop window matters more here.
Rain Showers Likely leaving Chesapeake and Chance Rain Showers near South Boston.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chesapeake to South Boston?
The road trip is about 164.6 miles (264.9 km) and usually takes 03h 41m in normal driving conditions.
Is this a same-day trip or an overnight route?
This is still possible in one day, but it becomes a long driving day. Leaving early and planning your stop window matters more here.
What is the halfway point on this route?
Emporia is a useful midpoint, sitting about 82.1 miles from Chesapeake and 82.4 miles from South Boston.
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 19 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 6:00 AM to 8:00 AM EDT. If you want a more comfortable same-day return, try to leave by 9:36 AM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $23.01 one way or $46.03 round trip. Estimated CO2 is about 51.6 kg one way.
What should you check before leaving?
Before you leave, expect Rain Showers Likely around Chesapeake and Chance Rain Showers near South Boston.
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 Chesapeake and South Boston. Straight-line distance: 145.62 mi (234.35 km).
#1 Chesapeake
The second most populous city in Virginia.
| Population | 247,011 |
| Coordinates | 36.8190400, -76.2749400 |
| Altitude | 3 |
| Country | United States |
#2 South Boston
Town in Halifax County, Virginia, United States
| Population | 7,519 |
| Coordinates | 36.6987500, -78.9014000 |
| Altitude | 131 |
| Country | United States |
End: South Boston (-78.9014, 36.69875)
Estimated Travel Time
Distance: 265 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 05h 29m |
| 40 mph (64.37 km/h) | 04h 06m |
| 50 mph (80.47 km/h) | 03h 17m |
| 60 mph (96.56 km/h) | 02h 44m |
| 70 mph (112.65 km/h) | 02h 21m |
| 80 mph (129 km/h) | 02h 03m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.96 | $23.01 | $46.03 |
| Mid-grade | $4.43 | $25.73 | $51.46 |
| Premium | $4.78 | $27.76 | $55.52 |
| Diesel | $5.62 | $32.68 | $65.35 |
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.