How far is Waukegan, IL from Windsor, IL?
The driving distance from Waukegan, IL to Windsor, IL is about 235.2 miles (378.5 km), with a travel time of about 04h 41m by car.
- The straight-line flight distance is about 205.7 miles (331 km).
- For a round trip, plan for roughly 09h 22m 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 41m.
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.
Township in Iroquois County, Illinois
Route Weather Snapshot
Check the forecast at both ends before you head out.
Mostly Sunny
Slight Chance Rain Showers
Driving Route Map
The map below follows the saved road route between Waukegan and Windsor.
Turn-by-Turn Driving Directions
Step-by-step road directions between Waukegan and Windsor.
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1
Start on North Jackson Street
2647 ft · 1 min · North Jackson Street
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2
Turn right onto Glen Rock Avenue
2495 ft · 1 min · Glen Rock Avenue
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3
Turn right onto Belvidere Street
1368 ft · 34 sec · Belvidere Street
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4
Turn left onto South Lewis Avenue
2.9 mi · 5 min · South Lewis Avenue
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5
Turn right onto Buckley Road
1.1 mi · 2 min · Buckley Road
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6
Turn left onto North Skokie Highway
5.6 mi · 7 min · North Skokie Highway
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7
Continue on Skokie Valley Road
3.4 mi · 4 min · Skokie Valley Road
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8
Continue on Skokie Highway
3.8 mi · 4 min · Skokie Highway
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9
Continue on Edens Expressway
13.7 mi · 17 min · Edens Expressway
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10
Continue on Kennedy Expressway
8.1 mi · 12 min · Kennedy Expressway
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11
Continue on Dan Ryan Expressway
2.4 mi · 3 min · Dan Ryan Expressway
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12
Keep slight left to continue on Dan Ryan Expressway (Express)
8.8 mi · 12 min · Dan Ryan Expressway (Express)
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13
Keep slight right to continue on I 57 South: Memphis
168.6 mi · 3 hr 6 min
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14
Take the exit slight right toward IL 16 West: Mattoon
2489 ft · 1 min
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15
Turn straight onto Charleston Avenue East
2.9 mi · 6 min · Charleston Avenue East
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16
Turn left onto South 21st Street
1164 ft · 24 sec · South 21st Street
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17
Turn right onto Marshall Avenue
1.6 mi · 3 min · Marshall Avenue
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18
Continue on Route 16
1.5 mi · 2 min · Route 16
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19
Continue on Marshall Avenue
1.8 mi · 3 min · Marshall Avenue
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20
Continue on Illinois Route 16
1.3 mi · 2 min · Illinois Route 16
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21
Continue on South 1st Street
5.2 mi · 8 min · South 1st Street
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22
Continue on Kentucky Avenue
1663 ft · 30 sec · Kentucky Avenue
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23
Turn right onto South Maple Street
1414 ft · 1 min · South Maple Street
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24
Arrive at your destination
0 m · 1 sec · North Maple Street
Car Route Details
A richer read on the saved driving route between Waukegan 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
Keep slight right to continue on I 57 South: Memphis
169 mi · 03h 06m
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 Waukegan and Slight Chance Rain Showers near Windsor.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Waukegan to Windsor?
The road trip is about 235.2 miles (378.5 km) and usually takes 04h 41m 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?
Ashkum is a useful midpoint, sitting about 117.6 miles from Waukegan and 117.6 miles from Windsor.
How much longer is the road route than the straight-line distance?
The direct path is about 205.7 miles (331 km), while the road route adds roughly 29.5 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 7:38 AM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $31.30 one way or $62.60 round trip. Estimated CO2 is about 73.8 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny around Waukegan and Slight Chance Rain Showers near Windsor.
Stop Ideas Near Ashkum
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 Ashkum.
Gilman
Kankakee
Dwight station
Pontiac station
Flight Path Map
This map shows the direct air route between Waukegan and Windsor. Straight-line distance: 205.7 mi (331.05 km).
#1 Waukegan
The second most populous city in Lake County, Illinois.
| Population | 85,453 |
| Coordinates | 42.3636300, -87.8447900 |
| Altitude | 199 |
| 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: 379 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 07h 50m |
| 40 mph (64.37 km/h) | 05h 52m |
| 50 mph (80.47 km/h) | 04h 42m |
| 60 mph (96.56 km/h) | 03h 55m |
| 70 mph (112.65 km/h) | 03h 21m |
| 80 mph (129 km/h) | 02h 56m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $31.30 | $62.60 |
| Mid-grade | $4.25 | $35.30 | $70.60 |
| Premium | $4.65 | $38.63 | $77.26 |
| Diesel | $5.30 | $44.02 | $88.05 |
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 11, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.