How far is Chesapeake, VA from Chester, VA?
The driving distance from Chesapeake, VA to Chester, VA is about 87.7 miles (141.2 km), with a travel time of about 02h 00m by car.
- The straight-line flight distance is about 74.3 miles (119.5 km).
- For a round trip, plan for roughly 04h 01m 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 00m.
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 Chesapeake and Chester.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chesapeake and Chester.
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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
1.9 mi · 3 min
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8
Take the exit slight right toward VA 164 West: Martin Luther King Jr Expressway, Norfolk
2001 ft · 38 sec
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9
Continue on Martin Luther King Jr Freeway
2723 ft · 48 sec · Martin Luther King Jr Freeway
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10
Continue on Martin Luther King Freeway
2952 ft · 56 sec · Martin Luther King Freeway
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11
Continue on Western Freeway
7.4 mi · 10 min · Western Freeway
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12
Continue on Bridge Road
6.5 mi · 11 min · Bridge Road
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13
Continue on Carrollton Boulevard
2.4 mi · 3 min · Carrollton Boulevard
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14
Turn left onto Brewers Neck Boulevard
2.9 mi · 4 min · Brewers Neck Boulevard
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15
Merge slight left onto Benns Church Boulevard
12.1 mi · 16 min · Benns Church Boulevard
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16
Continue on Colonial Trail East
9.9 mi · 11 min · Colonial Trail East
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17
Turn left onto Rolfe Highway
1 mi · 2 min · Rolfe Highway
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18
Turn right onto Colonial Trail West
13.3 mi · 15 min · Colonial Trail West
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19
Continue on James River Drive
14.6 mi · 19 min · James River Drive
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20
Continue on East Randolph Road
2.9 mi · 4 min · East Randolph Road
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21
Continue on East Hundred Road
8.9 mi · 15 min · East Hundred Road
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22
Turn left onto Winfree Street
82 m · 12 sec · Winfree Street
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23
Arrive at your destination
0 m · 1 sec · Winfree Street
Car Route Details
A richer read on the saved driving route between Chesapeake and Chester.
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.
Chance Light Rain leaving Chesapeake and Cloudy near Chester.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chesapeake to Chester?
The road trip is about 87.7 miles (141.2 km) and usually takes 02h 00m 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 43.8 miles from Chesapeake and 43.9 miles from Chester.
How much longer is the road route than the straight-line distance?
The direct path is about 74.3 miles (119.5 km), while the road route adds roughly 13.4 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 2:28 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $13.12 one way or $26.24 round trip. Estimated CO2 is about 27.5 kg one way.
What should you check before leaving?
Before you leave, expect Chance Light Rain around Chesapeake and Cloudy near Chester.
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 Chesapeake and Chester. Straight-line distance: 74.27 mi (119.52 km).
#1 Chesapeake
The second most populous city in Virginia.
| Population | 247,011 |
| Coordinates | 36.8190400, -76.2749400 |
| Altitude | 3 |
| Country | United States |
#2 Chester
Chester is a place in Virginia, United States.
| Population | 0 |
| Coordinates | 37.3568200, -77.4416500 |
| Altitude | 53 |
| Country | United States |
End: Chester (-77.44165, 37.35682)
Estimated Travel Time
Distance: 141 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 02h 55m |
| 40 mph (64.37 km/h) | 02h 11m |
| 50 mph (80.47 km/h) | 01h 45m |
| 60 mph (96.56 km/h) | 01h 27m |
| 70 mph (112.65 km/h) | 01h 15m |
| 80 mph (129 km/h) | 01h 05m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.23 | $13.12 | $26.24 |
| Mid-grade | $4.72 | $14.62 | $29.25 |
| Premium | $5.10 | $15.80 | $31.60 |
| Diesel | $6.39 | $19.79 | $39.59 |
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