How far is Naperville, IL from Windsor, IL?
The driving distance from Naperville, IL to Windsor, IL is about 206.9 miles (332.9 km), with a travel time of about 04h 01m by car.
- The straight-line flight distance is about 163.7 miles (263.5 km).
- For a round trip, plan for roughly 08h 03m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 8:00 AM CDT.
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 04h 01m.
An early departure helps you fit a real stop into the day without turning the return into a late-night drive.
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.
Village in Iroquois County, Illinois, United States of America
Route Weather Snapshot
Check the forecast at both ends before you head out.
Mostly Sunny
Mostly Sunny
Driving Route Map
The map below follows the saved road route between Naperville and Windsor.
Turn-by-Turn Driving Directions
Step-by-step road directions between Naperville and Windsor.
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1
Start on North Washington Street
15 m · 9 sec · North Washington Street
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2
Turn left onto East Ogden Avenue
5 mi · 10 min · East Ogden Avenue
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3
Take the ramp right toward I 355 Toll South: Joliet
1189 ft · 29 sec
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4
Merge slight left onto Veterans Memorial Tollway
19.2 mi · 22 min · Veterans Memorial Tollway
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5
Keep slight left to continue on I 80 East: Indiana
1.3 mi · 3 min
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6
Merge slight left
10.6 mi · 12 min
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7
Take the exit slight right toward I 57 South: Memphis
3222 ft · 1 min
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8
Merge slight left
154.4 mi · 2 hr 47 min
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9
Take the exit slight right toward IL 16 West: Mattoon
2489 ft · 1 min
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10
Turn straight onto Charleston Avenue East
2.9 mi · 6 min · Charleston Avenue East
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11
Turn left onto South 21st Street
1164 ft · 24 sec · South 21st Street
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12
Turn right onto Marshall Avenue
1.6 mi · 3 min · Marshall Avenue
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13
Continue on Route 16
1.5 mi · 2 min · Route 16
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14
Continue on Marshall Avenue
1.8 mi · 3 min · Marshall Avenue
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15
Continue on Illinois Route 16
1.3 mi · 2 min · Illinois Route 16
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16
Continue on South 1st Street
5.2 mi · 8 min · South 1st Street
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17
Continue on Kentucky Avenue
1663 ft · 30 sec · Kentucky Avenue
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18
Turn right onto South Maple Street
1414 ft · 1 min · South Maple Street
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19
Arrive at your destination
0 m · 1 sec · North Maple Street
Car Route Details
A richer read on the saved driving route between Naperville and Windsor.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
I 57 South
Merge slight left
154 mi · 02h 47m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A longer out-and-back drive
This is still possible in one day, but it becomes a long driving day. Leaving early and planning your stop window matters more here.
Mostly Sunny leaving Naperville and Mostly Sunny near Windsor.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Naperville to Windsor?
The road trip is about 206.9 miles (332.9 km) and usually takes 04h 01m in normal driving conditions.
Is this a same-day trip or an overnight route?
This is still possible in one day, but it becomes a long driving day. Leaving early and planning your stop window matters more here.
What is the halfway point on this route?
Onarga is a useful midpoint, sitting about 103.5 miles from Naperville and 103.4 miles from Windsor.
How much longer is the road route than the straight-line distance?
The direct path is about 163.7 miles (263.5 km), while the road route adds roughly 43.2 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 8:00 AM CDT. If you want a more comfortable same-day return, try to leave by 8:56 AM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $27.53 one way or $55.06 round trip. Estimated CO2 is about 64.9 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny around Naperville and Mostly Sunny near Windsor.
Stop Ideas Near Onarga
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 Onarga.
Gilman
Kankakee
Rantoul
Dwight station
Flight Path Map
This map shows the direct air route between Naperville and Windsor. Straight-line distance: 163.71 mi (263.47 km).
#1 Naperville
The second most populous city in Illinois.
| Population | 147,986 |
| Coordinates | 41.7858600, -88.1472900 |
| Altitude | 216 |
| Country | United States |
#2 Windsor
Town in Shelby County, Illinois, United States
| Population | 1,128 |
| Coordinates | 39.4408700, -88.5947800 |
| Altitude | 214 |
| Country | United States |
End: Windsor (-88.59478, 39.44087)
Estimated Travel Time
Distance: 333 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 06h 53m |
| 40 mph (64.37 km/h) | 05h 10m |
| 50 mph (80.47 km/h) | 04h 08m |
| 60 mph (96.56 km/h) | 03h 26m |
| 70 mph (112.65 km/h) | 02h 57m |
| 80 mph (129 km/h) | 02h 34m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $27.53 | $55.06 |
| Mid-grade | $4.25 | $31.05 | $62.09 |
| Premium | $4.65 | $33.97 | $67.95 |
| Diesel | $5.30 | $38.72 | $77.44 |
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 Illinois · Apr 23, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.