How far is Chester, VA from Portsmouth, VA?
The driving distance from Chester, VA to Portsmouth, VA is about 86.1 miles (138.5 km), with a travel time of about 01h 39m by car.
- The straight-line flight distance is about 72.6 miles (116.8 km).
- For a round trip, plan for roughly 03h 19m 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 01h 39m.
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.
Route Weather Snapshot
Check the forecast at both ends before you head out.
Chance Light Rain
Driving Route Map
The map below follows the saved road route between Chester and Portsmouth.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chester and Portsmouth.
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1
Start on Winfree Street
82 m · 16 sec · Winfree Street
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2
Turn right onto West Hundred Road
9 mi · 15 min · West Hundred Road
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3
Continue on West Randolph Road
2.9 mi · 4 min · West Randolph Road
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4
Continue on James River Drive
14.6 mi · 19 min · James River Drive
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5
Continue on Colonial Trail West
13.3 mi · 15 min · Colonial Trail West
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6
At the end of the road, turn left onto Rolfe Highway
1 mi · 2 min · Rolfe Highway
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7
Take the exit right
45 m · 6 sec
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8
Merge slight left onto Colonial Trail East
9.8 mi · 11 min · Colonial Trail East
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9
Continue on Old Stage Highway
12 mi · 16 min · Old Stage Highway
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10
Keep slight left to continue on Brewers Neck Boulevard
2.8 mi · 4 min · Brewers Neck Boulevard
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11
Take the exit slight right
713 ft · 20 sec
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12
Merge slight left onto Carrollton Boulevard
2.3 mi · 3 min · Carrollton Boulevard
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13
Continue on Bridge Road
6.2 mi · 11 min · Bridge Road
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14
Keep slight right to continue on Western Freeway
7.4 mi · 10 min · Western Freeway
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15
Merge slight left onto Martin Luther King Freeway
1.1 km · 46 sec · Martin Luther King Freeway
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16
Take the exit slight right toward VA 141 South: Downtown Portsmouth
1461 ft · 36 sec
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17
Turn straight onto London Boulevard
1.2 mi · 2 min · London Boulevard
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18
Turn right onto Effingham Street
552 ft · 11 sec · Effingham Street
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19
Turn left onto High Street
2679 ft · 1 min · High Street
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20
Continue on High Street
61 m · 21 sec · High Street
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21
Arrive at your destination
0 m · 1 sec · High Street
Car Route Details
A richer read on the saved driving route between Chester and Portsmouth.
Interchange-aware route
The drive includes several ramps, exits, or merges, so checking the next few maneuvers before busy interchanges is useful.
James River Drive
Continue on James River Drive
14.6 mi · 00h 19m
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.
Cloudy leaving Chester and Chance Light Rain near Portsmouth.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chester to Portsmouth?
The road trip is about 86.1 miles (138.5 km) and usually takes 01h 39m 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?
Surry is a useful midpoint, sitting about 42.2 miles from Chester and 43.9 miles from Portsmouth.
How much longer is the road route than the straight-line distance?
The direct path is about 72.6 miles (116.8 km), while the road route adds roughly 13.5 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 3:10 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $12.87 one way or $25.73 round trip. Estimated CO2 is about 27 kg one way.
What should you check before leaving?
Before you leave, expect Cloudy around Chester and Chance Light Rain near Portsmouth.
Stop Ideas Near Surry
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
James City County
James City County Government Center
Legacy Hall
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Surry.
Williamsburg Transportation Center
Newport News station
Petersburg station
Norfolk
Flight Path Map
This map shows the direct air route between Chester and Portsmouth. Straight-line distance: 72.58 mi (116.81 km).
#1 Chester
Chester is a place in Virginia, United States.
| Population | 0 |
| Coordinates | 37.3568200, -77.4416500 |
| Altitude | 53 |
| Country | United States |
#2 Portsmouth
The most populous city in Portsmouth, Virginia.
| Population | 95,094 |
| Coordinates | 36.8354300, -76.2982700 |
| Altitude | 3 |
| Country | United States |
End: High Street (-76.29827, 36.835429)
Estimated Travel Time
Distance: 139 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 02h 52m |
| 40 mph (64.37 km/h) | 02h 09m |
| 50 mph (80.47 km/h) | 01h 43m |
| 60 mph (96.56 km/h) | 01h 26m |
| 70 mph (112.65 km/h) | 01h 13m |
| 80 mph (129 km/h) | 01h 04m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.23 | $12.87 | $25.73 |
| Mid-grade | $4.72 | $14.34 | $28.68 |
| Premium | $5.10 | $15.49 | $30.98 |
| Diesel | $6.39 | $19.41 | $38.82 |
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 · Sep 24, 2026