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Trip from Sleepy Hollow, IL to Waukegan, IL

Drive Time

7h 1m

Distance

368.9 mi

594 km

Drive Score

8/10

Great drive

Same Day?

Yes, doable

Fuel Cost

$56

one way

EV Charging

Excellent

27 DC fast

Best Time to Leave

Save up to 33 min
4 AM
6h 51m ★
6 AM
7h 2m
8 AM
7h 24m
10 AM
7h 10m
12 PM
7h 7m
3 PM
7h 11m
5 PM
7h 23m
8 PM
6h 55m

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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Downtown Sleepy Hollow, IL, IL

Sleepy Hollow, IL

Stéphane Tendon

Trip Overview

The drive from Sleepy Hollow, IL to Waukegan, IL covers 368.9 miles and takes about 7h 1m behind the wheel. This route is realistic as a one-day drive if you keep your stops efficient.

The route leans on I 57, Ken Gray Expressway, Edens Expressway for much of the mileage, and the overall profile is highway-focused drive. The longest uninterrupted segment is about 195.2 miles on I 57. At current regular gas prices, budget about $56.03 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

2 planned breaks

Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.

Midpoint

184.5 miles from Sleepy Hollow, IL

A natural place for your longest stop of the day , about 3h 25m into the drive .

Drive Character

This is a 7h 1m highway drive covering 368.9 miles, with most of the trip on I 57 and Ken Gray Expressway. The longest continuous stretch is about 195.2 miles on I 57.

Most of the miles stay on highways, which makes pacing and fuel planning easier than turn-by-turn city driving.
There are about 22 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 195.2 miles.

How Hard Is This Drive?

This is a straightforward highway drive that stays mostly on I 57 and Ken Gray Expressway. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 2.2 miles in near Lake Egypt Road.

Route Complexity 7/10

Demanding - plan breaks and stay ahead of the key maneuvers

This is a demanding drive. With 14 significant decision points across 368.9 miles, you will need to stay alert — especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.

Where does it get tricky?

The main spots that need attention: at 2.2 miles (Lake Egypt Road): Navigation decision point; at 122.1 miles (I 57): Highway fork - watch signs carefully. Lane positioning matters here; at 320.6 miles (I 94 / Dan Ryan Expressway (Express)): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.

Critical Maneuvers

5 of 14 key points

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

5
2.2 mi into trip | ~5m in | Lake Egypt Road

At end of road, turn left onto Lake Egypt Road

Navigation decision point

7
122.1 mi into trip | ~2h 17m in | I 57

Keep slight left at fork onto I 57 toward I 57 North: Chicago

Highway fork - watch signs carefully. Lane positioning matters here

Use the straight / slight right lanes. Toward I 57 North: Chicago
8
320.6 mi into trip | ~5h 55m 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
350.2 mi into trip | ~6h 36m 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
365.7 mi into trip | ~6h 55m 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

Main Roads

Road Distance Duration
I 57 195.2 mi 3h 34m
Ken Gray Expressway 117.9 mi 2h 7m
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
Skokie Highway 3.8 mi 4m
Skokie Valley Road 3.4 mi 3m
Longest stretch: I 57 — 195.2 mi, about 3h 34m

Turn-by-Turn Driving Directions

Step-by-step road directions between Sleepy Hollow, IL and Waukegan, IL.

1

Start on Sleepy Hollow Lane

475 ft · 23 sec · Sleepy Hollow Lane
2

Turn right onto Power Plant Road

2.1 mi · 5 min · Power Plant Road
3

At end of road, turn left onto Lake Egypt Road

1.0 mi · 2 min · Lake Egypt Road
4

Turn left onto IL 37

0.3 mi · 31 sec · IL 37
5

At end of road, turn right onto IL 148

0.4 mi · 41 sec · IL 148
6

Take the ramp

0.3 mi · 37 sec
7

Merge onto I 57

50 mi · 54 min · Ken Gray Expressway
8

Keep slight right at fork onto I 57

67 mi · 1 hr 12 min · Ken Gray Expressway
Toward I 57 North: Chicago
9

Keep slight left at fork onto I 57

195 mi · 3 hr 34 min · I 57
Toward I 57 North: Chicago Use the straight / slight right lanes.
10

Continue on I 94

3.3 mi · 4 min · Dan Ryan Expressway
Use the straight / slight right lanes.
11

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 straight / slight right lanes.
12

Continue on I 90; I 94

8.2 mi · 11 min · Kennedy Expressway
Use the straight / slight right lanes.
13

Continue on I 94

14 mi · 17 min · Edens Expressway
Toward I 94 West: Milwaukee Use the straight / slight right lanes.
14

Keep slight left at fork onto US 41

3.8 mi · 4 min · Skokie Highway
Use the straight / slight right lanes.
15

Continue on US 41

3.4 mi · 3 min · Skokie Valley Road
16

Continue on US 41

8.2 mi · 10 min · South Skokie Highway
Use the left lane.
17

Take the exit

0.3 mi · 36 sec
Toward IL 120 East Use the straight / slight right lanes.
18

Turn straight onto IL 120

0.3 mi · 33 sec · Belvidere Road
19

Continue on IL 120

1.6 mi · 3 min · Belvidere Street
20

Turn left onto Glen Rock Avenue

0.5 mi · 1 min · Glen Rock Avenue
Use the left lane.
21

Turn left onto South Jackson Street

0.5 mi · 1 min · South Jackson Street
22

Arrive at destination

North Jackson Street

Trip Plan

Morning Departure

Start early — leave by 6-7 AM to arrive at a reasonable hour.

Evening Departure

This is a long drive — plan for a morning departure or consider splitting it into two days.

You can normally do this drive in one day.
Plan roughly 2 meaningful breaks for fuel, food, and rest.
The halfway point lands around 184.5 miles from Sleepy Hollow, IL, or about 3h 25m into the drive.
The longest continuous stretch on this route runs about 195.2 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 81 miles or 1h 32m in

Use this first pause for coffee, a restroom break, and a quick traffic check ahead.

Halfway reset

Around 184.5 miles or 3h 25m in

This is the best place for your longest stop, a real meal, and a full fuel check.

Final approach

Final hour starts around 5h 42m

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 Sleepy Hollow, 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.

+

Pick one backup stop option before the midpoint in case traffic changes your pacing.

Day 1

Settle into the route from Sleepy Hollow, IL

This is one driving day of about 368.9 miles and 7h 1m.

Your first comfortable stop window is around 81 miles from Sleepy Hollow, IL.
This route can stay practical as a one-day drive if traffic stays reasonable.
Plan about 2 real breaks rather than only quick fuel stops.
The longest stretch is on I 57 for about 195.2 miles.

Where to Stop

Rest stops, refuel points, and overnight suggestions along this route.

Halfway Point

Midpoint

About 184.5 mi from Sleepy Hollow, IL · 3h 25m into the drive

Mid-route town

Meal stop

Champaign, IL

184 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.

Popular next leg

Champaign, IL to Waukegan, IL

178.1 mi · 2h 55m

Pacing Suggestions

Plainfield, IL

Fuel and coffee

A short stop after about 81 miles helps settle the day before fatigue starts building.

Champaign, IL

Meal break

The midpoint is around 184.5 miles from Sleepy Hollow, 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 195.2 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.

National Parks Near This Route

Worth a detour if your schedule allows.

Pullman National Historical Park

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...

3 mi from route ~7 min detour Free near mile 318
Caution: Road Construction Near the Park
View on nps.gov

Park data from the National Park Service API. Alerts update every 2 hours.

Fuel & Cost

Regular Gas

$56.03 one way

$112.06 round trip

$3.86/gal 25.4 MPG avg 129 kg CO2
Fuel Type $/gal One Way Round Trip
midgrade $4.25 $61.77 $123.54
premium $4.80 $69.64 $139.28
diesel $5.64 $81.96 $163.91

No toll roads detected on this route.

Estimated Trip Cost (one way, 1 person)

Fuel

$56

Meals

$25–$50

Total

$81–$106

Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.

Estimated CO2 emission: 129.1 kg one way. Prices: EIA weekly data, 2026-04-06.

EV Charging Along Route

27 DC fast chargers · Coverage: excellent

Subway - Tesla Supercharger

Salem, IL

Tesla

12 DCFC

Holiday Inn - Tesla Supercharger

Effingham, IL

Tesla

12 DCFC

County Market - Tesla Supercharger

Champaign, IL

Tesla

12 DCFC

Mach 1 - Tesla Supercharger

Marion, IL

Tesla

8 DCFC

Mach 1 - Tesla Supercharger

Mt. Vernon, IL

Tesla

8 DCFC

Holiday Inn Mt. Vernon - Tesla Supercharger

Mt. Vernon, IL

Tesla

8 DCFC

Meijer - Tesla Supercharger

Champaign, IL

Tesla

8 DCFC

Jack Flash - Effingham - Tesla Supercharger

Effingham, IL

Tesla

6 DCFC

Tesla: 8 UNIVERSAL: 3 Electrify America: 3 ChargePoint Network: 3 eVgo Network: 2 RED_E: 2 Blink Network: 2 SYNERGEV: 1 CIRCLE_K: 1 Non-Networked: 1 FORD_CHARGE: 1

Station data from NREL Alternative Fuel Stations database.

Driving Electric?

About $39 in charging · 1 stop · 67% less CO2

Vehicle Type kWh Stops DC Fast Home Charge
Average EV 110.7 1 $38.73 $17.71
Efficient EV 92.2 1 $32.28 $14.76
EV Truck/SUV 147.6 1 $51.65 $23.61

Gas CO2

129 kg

EV CO2

43 kg (67% less)

Plan for 1 charging stop. A 30-minute DC fast charge mid-route should be enough to complete the trip comfortably.

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 1 day ago

Origin

Sleepy Hollow, IL

Morning in Sleepy Hollow on Monday

Local time

9:28 AM

CDT

Current temp

75°F

Unavailable

Live forecast

Destination

Waukegan, IL

Morning in Waukegan on Monday

Local time

9:28 AM

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

32 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

7h 1m on the road

Start early — leave by 6-7 AM to arrive at a reasonable hour.

Weather data from the National Weather Service. Conditions may change; check closer to your travel date.

Frequently Asked Questions

The drive from Sleepy Hollow, IL to Waukegan, IL covers 368.9 miles and takes about 7h 1m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are I 57, Ken Gray Expressway, Edens Expressway. Most of the drive stays on highways, so watch for ramps and exits.
This is a comfortable same-day trip.
The midpoint is about 184.5 miles from Sleepy Hollow, IL. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $56.03 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.
Start early — leave by 6-7 AM to arrive at a reasonable hour. This is a long drive — plan for a morning departure or consider splitting it into two days.
Plan about 2 meaningful breaks for fuel, food, or rest. Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
This is a demanding drive. With 14 significant decision points across 368.9 miles, you will need to stay alert — especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.
The main spots that need attention: at 2.2 miles (Lake Egypt Road): Navigation decision point; at 122.1 miles (I 57): Highway fork - watch signs carefully. Lane positioning matters here; at 320.6 miles (I 94 / Dan Ryan Expressway (Express)): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
The route from Sleepy Hollow, IL to Waukegan, IL does not surface many named destination signs beyond the main corridor.

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Explore More

Return Trip

Waukegan, IL to Sleepy Hollow, IL

Plan the drive back the other way.

368.7 mi 7h

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