Drive Time
4h 41m
Distance
235.2 mi
379 km
Drive Score
8/10
Great drive
Same Day?
Yes, doable
Fuel Cost
$35
one way
The drive from Waukegan, IL to Windsor, IL covers 235.2 miles and takes about 4h 41m behind the wheel. This route is realistic as a one-day drive if you keep your stops efficient.
The route leans on Glen Rock Avenue, Belvidere Street, South Lewis Avenue for much of the mileage, and the overall profile is turn-heavy local drive. At current regular gas prices, budget about $34.92 one way before food or hotel costs.
Trip Pace
Same-day drive is realistic
A same-day return is possible, but it will make for a full day on the road.
Break Rhythm
1 planned break
Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
Midpoint
117.6 miles from Waukegan, IL
A natural place for your longest stop of the day , about 2h 20m into the drive .
Expect a 4h 41m drive with frequent turns across 235.2 miles of local and secondary roads.
| Road | Distance | Duration |
|---|---|---|
| Glen Rock Avenue | Unavailable | Refreshing |
| Belvidere Street | Unavailable | Refreshing |
| South Lewis Avenue | Unavailable | Refreshing |
| Buckley Road | Unavailable | Refreshing |
| North Skokie Highway | Unavailable | Refreshing |
| Skokie Valley Road | Unavailable | Refreshing |
| Skokie Highway | Unavailable | Refreshing |
| Edens Expressway | Unavailable | Refreshing |
Per-road distance and duration are being refreshed from OSRM for this route.
Step-by-step road directions between Waukegan, IL and Windsor, IL.
Start on North Jackson Street
Turn right onto Glen Rock Avenue
Turn right onto Belvidere Street
Turn left onto South Lewis Avenue
Turn right onto Buckley Road
Turn left onto North Skokie Highway
Continue on Skokie Valley Road
Continue on Skokie Highway
Continue on Edens Expressway
Continue on Kennedy Expressway
Continue on Dan Ryan Expressway
Keep slight left to continue on Dan Ryan Expressway (Express)
Keep slight right to continue on I 57 South: Memphis
Take the exit slight right toward IL 16 West: Mattoon
Turn straight onto Charleston Avenue East
Turn left onto South 21st Street
Turn right onto Marshall Avenue
Continue on Route 16
Continue on Marshall Avenue
Continue on Illinois Route 16
Continue on South 1st Street
Continue on Kentucky Avenue
Turn right onto South Maple Street
Arrive at your destination
Morning Departure
An early start around 7-8 AM gets you there with plenty of daylight left.
Evening Departure
A late afternoon start means arriving after dark. Morning is better.
This is a comfortable same-day trip.
Departure
Before you leave
Start with fuel, water, and navigation already sorted so the first hour feels easy.
First stop
Around 80 miles or 1h 35m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 117.6 miles or 2h 20m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 3h 50m
Traffic, exits, and arrival timing usually matter more near Windsor, IL than in the middle of the route.
Open the route before leaving Waukegan, IL so your first major turns are already loaded.
Leave with enough water and a charging cable within reach, not packed away.
Check your fuel range against the first long segment, especially if you are starting outside city service areas.
Day 1
Settle into the route from Waukegan, IL
This is one driving day of about 235.2 miles and 4h 41m.
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 117.6 mi from Waukegan, IL · 2h 20m into the drive
Mid-route town
Meal stop
118 mi into the route
Best for: Lunch, fuel, and a longer reset
This sits close to the middle of the route, so it works well for the longest stop of the day.
The final approach into Windsor, IL usually feels slower than the middle of the drive, so avoid planning your tightest schedule at the very end.
Try to arrive with enough fuel left to skip an immediate station stop unless you already know the area around Windsor, IL.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
Regular Gas
$34.92 one way
$69.84 round trip
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.25 | $39.38 | $78.76 |
| premium | $4.65 | $43.10 | $86.19 |
| diesel | $5.30 | $49.11 | $98.23 |
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$35
Meals
$25–$50
Total
$60–$85
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 82.3 kg one way.
Driving Electric?
About $25 in charging · 0 stops · 66% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 70.6 | 0 | $24.70 | $11.29 |
| Efficient EV | 58.8 | 0 | $20.58 | $9.41 |
| EV Truck/SUV | 94.1 | 1 | $32.93 | $15.05 |
Gas CO2
82 kg
EV CO2
28 kg (66% less)
Plan for 0 charging stops, roughly every 270 miles. Allow 25-40 minutes per stop at a DC fast charger.
DC fast charging avg $0.35/kWh. Home charging avg $0.16/kWh. US grid CO2: 0.39 kg/kWh.
Travel Intel
Current conditions at both ends of the drive. If you're planning ahead, check the forecast closer to your travel date.
Origin
Morning in Waukegan on Saturday
Local time
9:30 AM
CDT
Current temp
43°F
Forecast unavailable right now
Destination
Morning in Windsor on Saturday
Local time
9:30 AM
CDT
Current temp
55°F
Forecast unavailable right now
Along the Route
53°F
Alsip, IL
118 mi in
Seasonal Notes
Summer travel usually means heavier construction, hotter rest stops, and busier weekend traffic around major cities.
Winter travel shortens daylight, so a route that looks manageable on paper can feel much longer after dark.
Holiday weekends tend to make both departure and arrival windows slower than the raw route time suggests.
Time zone
Origin and destination are on the same clock, so arrival timing is easier to judge at a glance.
Temperature spread
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
An early start around 7-8 AM gets you there with plenty of daylight left.
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