Trip from Windsor, IL to Waukegan, IL

Drive Time

4h 43m

Distance

236.2 mi

380 km

Drive Score

8/10

Great drive

Same Day?

Yes, doable

Fuel Cost

$36

one way

EV Charging

station data

Best Time to Leave

Save up to 40 min

4 AM

4h 30m ★

6 AM

4h 43m

8 AM

5h 10m

10 AM

4h 53m

12 PM

4h 50m

3 PM

4h 54m

5 PM

5h 9m

8 PM

4h 35m

Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.

Best Time Drive vs Fly

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Windsor, IL

Mike Tyurin

Trip Overview

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 .

Drive Character

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.

Most of the miles stay on highways, which makes pacing and fuel planning easier than turn-by-turn city driving.

There are about 24 navigation steps in the underlying route data, so the final approach matters more than the middle miles.

I 57 is the longest continuous segment at about 168.9 miles.

How Hard Is This Drive?

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.

Route Complexity 6/10

Moderate - straightforward overall, but long enough or busy enough to require pacing

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.

Critical Maneuvers

5 of 11 key points

These are the spots where you need to pay the most attention. Preview them before you drive.

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 none / straight / slight right lanes.

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 none lane. Toward I 90 Express, I 94 Express: Pershing Roa...

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 none / straight / slight right lanes.

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

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.

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.

Start on North Maple Street

0.3 mi · 1 min · North Maple Street

Turn left onto IL 16

0.3 mi · 28 sec · Kentucky Avenue

Continue on IL 16

5.2 mi · 7 min · Route 16

Continue on IL 16

1.3 mi · 1 min · Illinois Route 16

Continue on IL 16

1.8 mi · 2 min · Marshall Avenue

Continue on IL 16

1.5 mi · 2 min · Route 16

Continue on IL 16

1.6 mi · 3 min · Marshall Avenue

Turn left onto IL 16

0.2 mi · 20 sec · South 21st Street

Turn right onto IL 16

3.2 mi · 6 min · Charleston Avenue

Turn right

0.3 mi · 48 sec

Toward I-57 North: Champaign

Merge onto I 57

169 mi · 3 hr 6 min · I 57

Use the none / straight / slight right lanes.

Continue on I 94

3.3 mi · 4 min · Dan Ryan Expressway

Use the none / straight / slight right lanes.

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 Road Use the none lane.

Continue on I 90; I 94

8.2 mi · 11 min · Kennedy Expressway

Use the none / straight / slight right lanes.

Continue on I 94

14 mi · 17 min · Edens Expressway

Toward I 94 West: Milwaukee Use the none / straight / slight right lanes.

Keep slight left at fork onto US 41

3.8 mi · 4 min · Skokie Highway

Use the none / straight / slight right lanes.

Continue on US 41

3.4 mi · 3 min · Skokie Valley Road

Use the none lane.

Continue on US 41

8.2 mi · 10 min · South Skokie Highway

Use the none lane.

Take the exit

0.3 mi · 36 sec

Toward IL 120 East Use the straight / slight right lanes.

Turn straight onto IL 120

0.3 mi · 33 sec · Belvidere Road

Continue on IL 120

1.6 mi · 3 min · Belvidere Street

Use the none lane.

Turn left onto Glen Rock Avenue

0.5 mi · 1 min · Glen Rock Avenue

Use the left lane.

Turn left onto South Jackson Street

0.5 mi · 1 min · South Jackson Street

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 80 miles or 1h 37m 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 80 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.

Halfway Point

Midpoint

About 118.1 mi from Windsor, IL · 2h 19m into the drive

Mid-route town

Meal stop

Addison, IL

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.

Pacing Suggestions

Addison, IL

Fuel and coffee

A short stop after about 80 miles helps settle the day before fatigue starts building.

Addison, IL

Meal break

The midpoint is around 118.1 miles from Windsor, IL, which is a good place for a longer meal and fuel stop.

Before the longest stretch

Fuel check

Top up before I 57 if your tank is already low. That segment runs about 168.9 miles.

Arriving in Waukegan, IL

The final approach into Waukegan, 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 Waukegan, IL.

After long uninterrupted mileage, take five minutes before the last urban segment to reset and refocus on exits, merges, and city traffic.

These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.

Fuel & Cost

Regular Gas

$35.88 one way

$71.75 round trip

$3.86/gal 25.4 MPG avg 83 kg CO₂

Fuel Type	$/gal	One Way	Round Trip
midgrade	$4.25	$39.55	$79.10
premium	$4.80	$44.59	$89.18
diesel	$5.64	$52.48	$104.95

No toll roads detected on this route.

Estimated Trip Cost (one way, 1 person)

Fuel

$36

Meals

$25–$50

Total

$61–$86

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, 2026-04-06.

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 data refreshed 3 days ago

Origin

Windsor, IL

Evening in Windsor on Sunday

Local time

5:34 PM

CDT

Current temp

55°F

Unavailable

Live forecast

Destination

Waukegan, IL

Evening in Waukegan on Sunday

Local time

5:34 PM

CDT

Current temp

43°F

Unavailable

Live 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

12 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.

Frequently Asked Questions

The drive from Windsor, IL to Waukegan, IL covers 236.2 miles and takes about 4h 43m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.

The main roads are I 57, Edens Expressway, South Skokie Highway. Most of the drive stays on highways, so watch for ramps and exits.

This is a comfortable same-day trip.

The midpoint is about 118.1 miles from Windsor, IL. Look for rest areas, gas stations, or food options near the halfway mark.

At current regular gas prices, expect to spend about $35.88 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.

An early start around 7-8 AM gets you there with plenty of daylight left. A late afternoon start means arriving after dark. Morning is better.

Plan about 1 meaningful break for fuel, food, or rest. Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.

The route from Windsor, IL to Waukegan, IL does not surface many named destination signs beyond the main corridor.

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Return Trip

Waukegan, IL to Windsor, IL

Plan the drive back the other way.

235.2 mi 4h 41m

Explore more options from Windsor, IL or browse trips ending in Waukegan, IL.

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Trip from Windsor, IL to Waukegan, IL

Best Time to Leave

Trip Overview

Drive Character

How Hard Is This Drive?

Critical Maneuvers

Main Roads

Turn-by-Turn Driving Directions

Trip Plan

Before You Leave

Where to Stop

Pacing Suggestions

Arriving in Waukegan, IL

Fuel & Cost

Travel Intel

Windsor, IL

Waukegan, IL

Same local time

12 degrees cooler at arrival

4h 43m on the road

Frequently Asked Questions

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