How far is Chesapeake, VA from Windsor, VA?
The driving distance from Chesapeake, VA to Windsor, VA is about 30.3 miles (48.8 km), with a travel time of about 00h 45m by car.
- The straight-line flight distance is about 26 miles (41.8 km).
- For a round trip, plan for roughly 01h 31m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 8:00 AM to 10:00 AM EST.
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 00h 45m.
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.
The most populous city in Suffolk County, Virginia.
Route Weather Snapshot
Check the forecast at both ends before you head out.
Areas Of Frost then Sunny
Driving Route Map
The map below follows the saved road route between Chesapeake and Windsor.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chesapeake and Windsor.
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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
8.2 mi · 10 min · Portsmouth Boulevard
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14
Take the exit slight right toward US 460: Petersburg
1187 ft · 29 sec
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15
Keep slight right to continue on US 460 West: Petersburg, Albert G Horton Junior Memorial, Veterans Cemetery
8.4 mi · 14 min
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16
Arrive at your destination
0 m · 1 sec · East Windsor Boulevard
Car Route Details
A richer read on the saved driving route between Chesapeake and Windsor.
Turn-heavy local drive
The route has frequent decision points for its length, so lane choice and turn timing will matter more than cruising speed.
US 460 West
Keep slight right to continue on US 460 West: Petersburg, Albert G Horton Junior Memorial, Veterans Cemetery
8.37 mi · 00h 14m
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.
Sunny leaving Chesapeake and Areas Of Frost then Sunny near Windsor.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chesapeake to Windsor?
The road trip is about 30.3 miles (48.8 km) and usually takes 00h 45m 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?
Suffolk is a useful midpoint, sitting about 15.1 miles from Chesapeake and 15.2 miles from Windsor.
How much longer is the road route than the straight-line distance?
The direct path is about 26 miles (41.8 km), while the road route adds roughly 4.3 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 EST. If you want a more comfortable same-day return, try to leave by 4:58 PM EST.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $4.13 one way or $8.26 round trip. Estimated CO2 is about 9.5 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Chesapeake and Areas Of Frost then Sunny near Windsor.
Stop Ideas Near Suffolk
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Chartreuse Bistro
MacArthur Center Parking Garage
Smooth: A Skin & Waxing Boutique
Chesapeake City Hall
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Suffolk.
Norfolk
Newport News station
Virginia Beach, Virginia
Williamsburg Transportation Center
Flight Path Map
This map shows the direct air route between Chesapeake and Windsor. Straight-line distance: 25.96 mi (41.78 km).
#1 Chesapeake
The second most populous city in Virginia.
| Population | 247,011 |
| Coordinates | 36.8190400, -76.2749400 |
| Altitude | 3 |
| Country | United States |
#2 Windsor
Windsor is a place in Virginia, United States.
| Population | 0 |
| Coordinates | 36.8084800, -76.7441200 |
| Altitude | 24 |
| Country | United States |
End: Windsor (-76.74412, 36.80848)
Estimated Travel Time
Distance: 49 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 01h 00m |
| 40 mph (64.37 km/h) | 00h 45m |
| 50 mph (80.47 km/h) | 00h 36m |
| 60 mph (96.56 km/h) | 00h 30m |
| 70 mph (112.65 km/h) | 00h 25m |
| 80 mph (129 km/h) | 00h 22m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.86 | $4.13 | $8.26 |
| Mid-grade | $4.35 | $4.66 | $9.31 |
| Premium | $4.77 | $5.10 | $10.21 |
| Diesel | $6.16 | $6.59 | $13.18 |
Assumes 8.3 L/100 km (about 28.3 MPG). CO2 is an estimate and varies by vehicle, fuel blend, traffic, and terrain.
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