How far is Chester, VA from Chesapeake, VA?
The driving distance from Chester, VA to Chesapeake, VA is about 89.3 miles (143.7 km), with a travel time of about 01h 44m by car.
- The straight-line flight distance is about 74.3 miles (119.5 km).
- For a round trip, plan for roughly 03h 28m 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 44m.
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 Chesapeake.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chester and Chesapeake.
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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
1.4 km · 1 min · London Boulevard
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18
Turn right onto Elm Avenue
2.4 mi · 4 min · Elm Avenue
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19
Continue on South Norfolk Jordan Bridge
1.1 mi · 2 min · South Norfolk Jordan Bridge
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20
Turn straight onto Poindexter Street
1.1 km · 1 min · Poindexter Street
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21
Turn left onto D Street
126 m · 18 sec · D Street
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22
Arrive at your destination
0 m · 1 sec · D Street
Car Route Details
A richer read on the saved driving route between Chester and Chesapeake.
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 Chesapeake.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chester to Chesapeake?
The road trip is about 89.3 miles (143.7 km) and usually takes 01h 44m 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 43.9 miles from Chester and 45.5 miles from Chesapeake.
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 15 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 3:02 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $13.33 one way or $26.66 round trip. Estimated CO2 is about 28 kg one way.
What should you check before leaving?
Before you leave, expect Cloudy around Chester and Chance Light Rain near Chesapeake.
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 Chesapeake. Straight-line distance: 74.27 mi (119.52 km).
#1 Chester
Chester is a place in Virginia, United States.
| Population | 0 |
| Coordinates | 37.3568200, -77.4416500 |
| Altitude | 53 |
| 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: 144 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 02h 58m |
| 40 mph (64.37 km/h) | 02h 13m |
| 50 mph (80.47 km/h) | 01h 47m |
| 60 mph (96.56 km/h) | 01h 29m |
| 70 mph (112.65 km/h) | 01h 16m |
| 80 mph (129 km/h) | 01h 06m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.23 | $13.33 | $26.66 |
| Mid-grade | $4.72 | $14.86 | $29.72 |
| Premium | $5.10 | $16.05 | $32.10 |
| Diesel | $6.39 | $20.11 | $40.23 |
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