How far is Windsor, VA from Chesapeake, VA?
The driving distance from Windsor, VA to Chesapeake, VA is about 31.1 miles (50.1 km), with a travel time of about 00h 36m by car.
- The straight-line flight distance is about 26 miles (41.8 km).
- For a round trip, plan for roughly 01h 12m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 7:00 AM to 7:00 PM EST.
Reverse, save, or send this route
This is an easy same-day return drive. Copy the route link, send it to another device, or print a clean version before you head out.
This is an easy same-day return drive.
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 36m.
This is a short drive, so your comfort window is wide. Traffic and current weather matter more than the clock.
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
Sunny
Driving Route Map
The map below follows the saved road route between Windsor and Chesapeake.
Turn-by-Turn Driving Directions
Step-by-step road directions between Windsor and Chesapeake.
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1
Start on East Windsor Boulevard
1.3 km · 2 min · East Windsor Boulevard
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2
Continue on Windsor Boulevard
2.5 mi · 4 min · Windsor Boulevard
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3
Continue on Pruden Boulevard
5.1 mi · 9 min · Pruden Boulevard
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4
Take the exit straight toward US 58 West, US 460 East: Newport News, Norfolk, Virginia Beach
10.5 mi · 13 min
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5
Take the exit slight right toward I 264 East, I 64, US 13 North: Portsmouth, Norfolk, Va Beach
1.2 km · 2 min
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6
Keep slight left to continue on I 264 East, I 64, US 13 North: Portsmouth, Norfolk, Va Beach
2322 ft · 57 sec
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7
Merge slight left onto Hampton Roads Beltway
3026 ft · 43 sec · Hampton Roads Beltway
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8
Take the exit slight left toward I 264 East: Portsmouth, Norfolk
1.2 km · 1 min
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9
Continue straight
3.7 mi · 5 min
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10
Take the exit slight right toward VA 164 West, US 17: Martin Luther King Jr Expressway, Norfolk, Frederick Boulevard
920 ft · 23 sec
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11
Keep slight right to continue on US 17: Frederick Boulevard
1070 ft · 28 sec
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12
Turn right onto Frederick Boulevard
1.2 mi · 2 min · Frederick Boulevard
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13
At the end of the road, turn left onto George Washington Highway
1964 ft · 50 sec · George Washington Highway
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14
Turn right onto Elm Avenue
1.3 km · 1 min · Elm Avenue
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15
Continue on South Norfolk Jordan Bridge
1.1 mi · 2 min · South Norfolk Jordan Bridge
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16
Turn straight onto Poindexter Street
1.1 km · 1 min · Poindexter Street
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17
Turn left onto D Street
126 m · 18 sec · D Street
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18
Arrive at your destination
0 m · 1 sec · D Street
Car Route Details
A richer read on the saved driving route between Windsor and Chesapeake.
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 58 West
Take the exit straight toward US 58 West, US 460 East: Newport News, Norfolk, Virginia Beach
10.5 mi · 00h 13m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A short regional drive
This route is short enough to handle as a quick errand, commute, or easy same-day return without much planning overhead.
Areas Of Frost then Sunny leaving Windsor and Sunny near Chesapeake.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Windsor to Chesapeake?
The road trip is about 31.1 miles (50.1 km) and usually takes 00h 36m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route is short enough to handle as a quick errand, commute, or easy same-day return without much planning overhead.
What is the halfway point on this route?
Suffolk is a useful midpoint, sitting about 14.9 miles from Windsor and 16.3 miles from Chesapeake.
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 5.1 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 7:00 AM to 7:00 PM EST. If you want a more comfortable same-day return, try to leave by 7:18 PM EST.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $4.25 one way or $8.49 round trip. Estimated CO2 is about 9.8 kg one way.
What should you check before leaving?
Before you leave, expect Areas Of Frost then Sunny around Windsor and Sunny near Chesapeake.
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 Windsor and Chesapeake. Straight-line distance: 25.96 mi (41.78 km).
#1 Windsor
Windsor is a place in Virginia, United States.
| Population | 0 |
| Coordinates | 36.8084800, -76.7441200 |
| Altitude | 24 |
| 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: 50 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 01h 02m |
| 40 mph (64.37 km/h) | 00h 46m |
| 50 mph (80.47 km/h) | 00h 37m |
| 60 mph (96.56 km/h) | 00h 31m |
| 70 mph (112.65 km/h) | 00h 26m |
| 80 mph (129 km/h) | 00h 23m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.86 | $4.25 | $8.49 |
| Mid-grade | $4.35 | $4.79 | $9.57 |
| Premium | $4.77 | $5.25 | $10.49 |
| Diesel | $6.16 | $6.77 | $13.55 |
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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