How far is Chesapeake, VA from Hillsville, VA?
The driving distance from Chesapeake, VA to Hillsville, VA is about 290.5 miles (467.5 km), with a travel time of about 06h 26m by car.
- The straight-line flight distance is about 246.8 miles (397.2 km).
- For a round trip, plan for roughly 12h 52m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 7:30 AM EDT.
Reverse, save, or send this route
This drive is better planned with a longer stop or an overnight stay. Copy the route link, send it to another device, or print a clean version before you head out.
This drive is better planned with a longer stop or an overnight stay.
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 06h 26m.
Starting early still helps, but most travelers will want a longer stop or an overnight stay on a route this long.
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.
Town in Virginia, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Showers And Thunderstorms
Occasional Showers And Thunderstorms
Driving Route Map
The map below follows the saved road route between Chesapeake and Hillsville.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chesapeake and Hillsville.
-
1
Start on D Street
126 m · 21 sec · D Street
-
2
At the end of the road, turn right onto Poindexter Street
1617 ft · 29 sec · Poindexter Street
-
3
Take the ramp straight toward I 464 North
1284 ft · 18 sec
-
4
Merge slight left
1.2 mi · 1 min
-
5
Keep slight right to continue on I 264 West Toll: Downtown Tunnel, Portsmouth
580 ft · 14 sec
-
6
Keep slight left to continue on I 264 West Toll: Tunnel
2569 ft · 1 min
-
7
Merge slight left
6.7 mi · 10 min
-
8
Keep slight right to continue on I 664: Bowers Hill, Suffolk, Richmond
1 km · 47 sec
-
9
Merge slight left onto Hampton Roads Beltway
2197 ft · 31 sec · Hampton Roads Beltway
-
10
Take the exit slight right toward US 13, US 58, US 460, VA 191 North: Suffolk, Military Highway
1598 ft · 54 sec
-
11
Keep slight left
3155 ft · 1 min
-
12
Continue on West Military Highway
2.4 mi · 3 min · West Military Highway
-
13
Continue on Portsmouth Boulevard
62.1 mi · 1 hr 21 min · Portsmouth Boulevard
-
14
Continue on Courtland Road
5.2 mi · 7 min · Courtland Road
-
15
Continue on Pleasant Shade Drive
6.3 mi · 9 min · Pleasant Shade Drive
-
16
Continue on Governor Harrison Parkway
22.5 mi · 30 min · Governor Harrison Parkway
-
17
Continue on Piney Pond Road
1.2 mi · 2 min · Piney Pond Road
-
18
Continue on Highway 58
3.5 mi · 5 min · Highway 58
-
19
Continue on East Atlantic Street
1.1 mi · 2 min · East Atlantic Street
-
20
Continue on South Hill Bypass
3.5 mi · 5 min · South Hill Bypass
-
21
Continue on Highway 1
3.2 mi · 4 min · Highway 1
-
22
Continue on Highway 58
18.9 mi · 24 min · Highway 58
-
23
Turn straight onto Clarksville Bypass
4 mi · 5 min · Clarksville Bypass
-
24
Continue on Highway 58
18.8 mi · 24 min · Highway 58
-
25
Continue on Philpott Road
19.7 mi · 26 min · Philpott Road
-
26
Continue on South Boston Highway
5.3 mi · 7 min · South Boston Highway
-
27
Continue on South Boston Road
3.1 mi · 5 min · South Boston Road
-
28
Take the ramp slight right toward US 29 South, US 58 West: Greesboro, Martinsville
1602 ft · 39 sec
-
29
Merge slight left onto Danville Expressway
13.9 mi · 16 min · Danville Expressway
-
30
Keep slight left
15.2 mi · 20 min
-
31
Take the exit straight toward US 58 West: Stuart, Roanoke
10.3 mi · 12 min
-
32
Take the exit slight right toward US 58 West: Stuart
55.1 mi · 1 hr 13 min
-
33
Continue on Hillsville Bypass
2.2 mi · 3 min · Hillsville Bypass
-
34
Take the exit slight right toward US 52: Fancy Gap, Hillsville
1198 ft · 33 sec
-
35
Turn right onto South Main Street
1.3 mi · 2 min · South Main Street
-
36
Turn left onto West Stuart Drive
22 m · 3 sec · West Stuart Drive
-
37
Arrive at your destination
0 m · 1 sec · West Stuart Drive
Car Route Details
A richer read on the saved driving route between Chesapeake and Hillsville.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
Portsmouth Boulevard
Continue on Portsmouth Boulevard
62.1 mi · 01h 21m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
Better with a longer stop
This route is long enough that most travelers will be better off planning an overnight stay or a more deliberate stop window.
Showers And Thunderstorms leaving Chesapeake and Occasional Showers And Thunderstorms near Hillsville.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chesapeake to Hillsville?
The road trip is about 290.5 miles (467.5 km) and usually takes 06h 26m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route is long enough that most travelers will be better off planning an overnight stay or a more deliberate stop window.
What is the halfway point on this route?
Clarksville is a useful midpoint, sitting about 145 miles from Chesapeake and 145.5 miles from Hillsville.
How much longer is the road route than the straight-line distance?
The direct path is about 246.8 miles (397.2 km), while the road route adds roughly 43.7 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 6:00 AM to 7:30 AM EDT. Starting early still helps, but most travelers will want a longer stop or an overnight stay on a route this long.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $40.60 one way or $81.20 round trip. Estimated CO2 is about 91.1 kg one way.
What should you check before leaving?
Before you leave, expect Showers And Thunderstorms around Chesapeake and Occasional Showers And Thunderstorms near Hillsville.
Stop Ideas Near Clarksville
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Clarksville.
Danville
Durham
North Carolina State Fair station
Cary
Flight Path Map
This map shows the direct air route between Chesapeake and Hillsville. Straight-line distance: 246.78 mi (397.15 km).
#1 Chesapeake
The second most populous city in Virginia.
| Population | 247,011 |
| Coordinates | 36.8190400, -76.2749400 |
| Altitude | 3 |
| Country | United States |
#2 Hillsville
Town in Carroll County, Virginia, United States
| Population | 2,686 |
| Coordinates | 36.7626300, -80.7347900 |
| Altitude | 767 |
| Country | United States |
End: Hillsville (-80.73479, 36.76263)
Estimated Travel Time
Distance: 468 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 09h 40m |
| 40 mph (64.37 km/h) | 07h 15m |
| 50 mph (80.47 km/h) | 05h 48m |
| 60 mph (96.56 km/h) | 04h 50m |
| 70 mph (112.65 km/h) | 04h 09m |
| 80 mph (129 km/h) | 03h 37m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.96 | $40.60 | $81.20 |
| Mid-grade | $4.43 | $45.40 | $90.79 |
| Premium | $4.78 | $48.97 | $97.95 |
| Diesel | $5.62 | $57.65 | $115.29 |
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 · May 25, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.