Traveling from Windsor to Waukegan covers 236.2 miles across the Illinois landscape, typically taking about 4 hours and 43 minutes of driving time. Because this journey is manageable within a single day, you likely won't need to book an overnight stay unless you prefer a slower pace. Budgeting roughly $36 for fuel will get you from the heart of the Midwest to your destination efficiently. The route utilizes a heavy reliance on major thoroughfares, making it a straightforward connection between these two points. By prioritizing highway travel, this itinerary offers a practical approach for drivers looking to minimize complexity while navigating the state.
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
118.1 miles from Windsor, IL
A natural place for your longest stop of the day
, about 2h 19m into the drive
.
Main Roads
Road
Distance
Duration
I 57
168.9 mi
3h 6m
Edens Expressway
13.5 mi
17m
South Skokie Highway
8.2 mi
10m
Kennedy Expressway
8.2 mi
11m
Dan Ryan Expressway (Express)
7.9 mi
11m
Route 16
6.7 mi
9m
Skokie Highway
3.8 mi
4m
Marshall Avenue
3.4 mi
5m
Longest stretch:
I 57
— 168.9 mi, about 3h 6m
Turn-by-Turn Driving Directions
Step-by-step road directions between Windsor, IL and Waukegan, IL.
1
Start on North Maple Street
0.3 mi·1 min·North Maple Street
2
Turn left onto IL 16
0.3 mi·28 sec·Kentucky Avenue
3
Continue on IL 16
5.2 mi·7 min·Route 16
4
Continue on IL 16
1.3 mi·1 min·Illinois Route 16
5
Continue on IL 16
1.8 mi·2 min·Marshall Avenue
6
Continue on IL 16
1.5 mi·2 min·Route 16
7
Continue on IL 16
1.6 mi·3 min·Marshall Avenue
8
Turn left onto IL 16
0.2 mi·20 sec·South 21st Street
9
Turn right onto IL 16
3.2 mi·6 min·Charleston Avenue
10
Turn right
0.3 mi·48 sec
Toward I-57 North: Champaign
11
Merge onto I 57
169 mi·3 hr 6 min·I 57
Use the straight / slight right lanes.
12
Continue on I 94
3.3 mi·4 min·Dan Ryan Expressway
Use the straight / slight right lanes.
13
Keep slight left at fork onto I 94
7.9 mi·11 min·Dan Ryan Expressway (Express)
Toward I 90 Express, I 94 Express: Pershing RoadUse the straight / slight right lanes.
14
Continue on I 90; I 94
8.2 mi·11 min·Kennedy Expressway
Use the straight / slight right lanes.
15
Continue on I 94
14 mi·17 min·Edens Expressway
Toward I 94 West: MilwaukeeUse the straight / slight right lanes.
16
Keep slight left at fork onto US 41
3.8 mi·4 min·Skokie Highway
Use the straight / slight right lanes.
17
Continue on US 41
3.4 mi·3 min·Skokie Valley Road
18
Continue on US 41
8.2 mi·10 min·South Skokie Highway
Use the left lane.
19
Take the exit
0.3 mi·36 sec
Toward IL 120 EastUse the straight / slight right lanes.
20
Turn straight onto IL 120
0.3 mi·33 sec·Belvidere Road
21
Continue on IL 120
1.6 mi·3 min·Belvidere Street
22
Turn left onto Glen Rock Avenue
0.5 mi·1 min·Glen Rock Avenue
Use the left lane.
23
Turn left onto South Jackson Street
0.5 mi·1 min·South Jackson Street
24
Arrive at destination
North Jackson Street
Trip Plan
Given the nearly five-hour duration, departing early in the morning is your best strategy to avoid mid-day congestion on the busier stretches of the Edens Expressway. Plan for at least one dedicated stop to stretch your legs and refuel, as the long initial segment on I-57 can be taxing if you stay behind the wheel for the entire duration. Keep a close watch on your fuel gauge during that long 168.9-mile interstate run to ensure you aren't caught off guard between service exits. Since this is a one-day trip, your primary advantage is flexibility, so feel free to time your stop to coincide with your preferred meal schedule. Having your route mapped out before hitting the major expressways will help you stay composed during the final urban approach.
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.
You can normally do this drive in one day.
Plan roughly 1 meaningful break for fuel, food, and rest.
The halfway point lands around 118.1 miles from Windsor, IL, or about 2h 19m into the drive.
The longest continuous stretch on this route runs about 168.9 miles.
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 52 miles or 1h 6m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 118.1 miles or 2h 19m 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 45m
Traffic, exits, and arrival timing usually matter more near Waukegan, IL than in the middle of the route.
Before You Leave
+
Open the route before leaving Windsor, 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 Windsor, IL
This is one driving day of about 236.2 miles and 4h 43m.
Your first comfortable stop window is around 52 miles from Windsor, IL.
This route can stay practical as a one-day drive if traffic stays reasonable.
Plan about 1 real break rather than only quick fuel stops.
The longest stretch is on I 57 for about 168.9 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 11
5 decision points cluster between mile 15.7 and 235.3 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
5
15.7 mi into trip|~26m in|I 57
Merge onto I 57
Merge point - match speed before joining. Lane positioning matters here
Use the straight / slight right lanes.
8
188 mi into trip|~3h 37m in|I 94 / Dan Ryan Expressway (Express)
Keep slight left at fork onto I 94 / Dan Ryan Expressway (Express) toward I 90 Express, I 94 Express: Pershing Road
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Toward I 90 Express, I 94 Express: Pershing Roa...
6
217.6 mi into trip|~4h 17m in|US 41 / Skokie Highway
Keep slight left at fork onto US 41 / Skokie Highway
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
6
233 mi into trip|~4h 36m in
Take the exit toward IL 120 East
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the straight / slight right lanes.
Toward IL 120 East
5
235.3 mi into trip|~4h 40m in|Glen Rock Avenue
Turn left onto Glen Rock Avenue
Lane positioning matters here
Use the left lane.
Fuel & Cost
Regular Gas
$36.93 one way
$73.85 round trip
$3.97/gal25.4 MPG avg83 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.36
$40.54
$81.09
premium
$4.89
$45.45
$90.91
diesel
$5.61
$52.15
$104.30
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$37
Meals
$25–$50
Total
$62–$87
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 82.6 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $25 in charging
· 0 stops
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
70.9
0
$24.80
$11.34
Efficient EV
59.1
0
$20.67
$9.45
EV Truck/SUV
94.5
1
$33.07
$15.12
Gas CO2
83 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.
Forecast as of Apr 18, 2026
Origin
Windsor, IL
Morning
in Windsor on Tuesday
Local time
7:50 AM
CDT
Current temp
51°F
Unavailable
Live forecast
Destination
Waukegan, IL
Morning
in Waukegan on Tuesday
Local time
7:50 AM
CDT
Current temp
42°F
Showers And Thunderstorms
SW 15 to 20 mph100% chanceLive forecast
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
Same local time
Origin and destination are on the same clock, so arrival timing is easier to judge at a glance.
Temperature spread
9 degrees cooler at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
4h 43m on the road
An early start around 7-8 AM gets you there with plenty of daylight left.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
National Parks Near This Route
Worth a detour if your schedule allows.
Pullman National Historical Park
National Historical Park
In a growing Chicago neighborhood, diverse people and stories intertwined. All were seeking opportunity. Some succeeded. Others were limited—by race, gender, or economic status. Their stories came tog...
4 mi from route
~9 min detour
Free
near mile 179.2
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
Expect a focused interstate experience, as 89% of this trip is spent on highways. The journey is dominated by a substantial 168.9-mile stretch on I-57, which sets the tone for a consistent, high-speed pace. As you transition onto the Edens Expressway and South Skokie Highway, the road environment shifts to accommodate the denser traffic patterns of the approach to Waukegan. This is a classic highway-focused drive, meaning you should prepare for a steady, rhythmic cruise rather than technical or winding secondary roads. It is a no-nonsense route designed for getting you from point A to point B with minimal deviation.
89% highway — fuel and pacing are the main things to plan.
24 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 168.9 mi on I 57.
How Hard Is This Drive?
6/10
This is a straightforward highway drive that stays mostly on I 57 and Edens Expressway. You will hit about 11 points where you need to pay attention to lane position or signs. The trickiest moment comes around 15.7 miles in near I 57.
Driving Effort6/10
Moderate - straightforward overall, but long enough or busy enough to require pacing
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 236.2 miles you will encounter 11 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.
Where does it get tricky?
The main spots that need attention: at 15.7 miles (I 57): Merge point - match speed before joining. Lane positioning matters here; at 188 miles (I 94 / Dan Ryan Expressway (Express)): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 217.6 miles (US 41 / Skokie Highway): Highway fork - watch signs carefully. Lane positioning matters here.
Waukegan is in the Far North Suburbs of the Chicagoland region of Illinois. It sits on Lake Michigan, has a large harbor, and is the county seat of Lake County, Illinois.
Doable as a same-day drive at 4h 43m. Total distance: 236.2 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
4h 43m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (89%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 168.9 miles on I 57. The full list of main roads is in the Roads section above.
We did not find dedicated rest areas on this route. For a drive this long, plan bathroom and stretch breaks around gas stations, fast-food stops, or small-town downtowns — check the Nearby Places section for options.
It helps. This route has a higher-than-average number of complex decision points, which get harder in the dark. If the last hour of the trip is on surface roads or mountain grades, aim to arrive at Waukegan, IL before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Only with planning. This is a long drive for kids — consider splitting it into two days rather than pushing through. Plan at least 1 meaningful breaks. Dedicated rest areas are limited, so plan gas or food stops as your bathroom breaks.
The main spots that need attention: at 15.7 miles (I 57): Merge point - match speed before joining. Lane positioning matters here; at 188 miles (I 94 / Dan Ryan Expressway (Express)): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 217.6 miles (US 41 / Skokie Highway): Highway fork - watch signs carefully. Lane positioning matters here.
Yes — Pullman National Historical Park. See the National Parks section for detour distances and tips on detours.
Possible but tiring. At 4.7 hours each way, an in-and-out day trip would put you behind the wheel for 9.4 hours — manageable with a long break at Waukegan, IL, but most travelers stay overnight.
