How far is Sleepy Hollow, IL from Waukegan, IL?
The driving distance from Sleepy Hollow, IL to Waukegan, IL is about 373.1 miles (600.4 km), with a travel time of about 05h 57m by car.
- The straight-line flight distance is about 334.2 miles (537.9 km).
- For a round trip, plan for roughly 11h 54m 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 05h 57m.
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.
City in Illinois, United States of America
Route Weather Snapshot
Check the forecast at both ends before you head out.
Sunny
Mostly Sunny
Driving Route Map
The map below follows the saved road route between Sleepy Hollow and Waukegan.
Turn-by-Turn Driving Directions
Step-by-step road directions between Sleepy Hollow and Waukegan.
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1
Start on Sleepy Hollow Lane
145 m · 23 sec · Sleepy Hollow Lane
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2
Turn right onto Power Plant Road
2.1 mi · 5 min · Power Plant Road
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3
At the end of the road, turn left onto Lake Egypt Road
1.5 km · 2 min · Lake Egypt Road
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4
Turn left
1753 ft · 32 sec
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5
At the end of the road, turn right
2311 ft · 41 sec
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6
Take the ramp right
1538 ft · 37 sec
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7
Merge slight left onto Ken Gray Expressway
50.5 mi · 54 min · Ken Gray Expressway
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8
Keep slight right to continue on Ken Gray Expressway
67.5 mi · 1 hr 13 min · Ken Gray Expressway
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9
Keep slight left to continue on I 57 North: Chicago
195.2 mi · 3 hr 34 min
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10
Continue on Dan Ryan Expressway
3.3 mi · 5 min · Dan Ryan Expressway
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11
Keep slight left to continue on Dan Ryan Expressway (Express)
7.9 mi · 11 min · Dan Ryan Expressway (Express)
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12
Continue on Kennedy Expressway
8.2 mi · 12 min · Kennedy Expressway
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13
Continue on Edens Expressway
13.5 mi · 17 min · Edens Expressway
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14
Keep slight left to continue on Skokie Highway
3.8 mi · 4 min · Skokie Highway
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15
Continue on Skokie Valley Road
3.4 mi · 4 min · Skokie Valley Road
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16
Continue on South Skokie Highway
8.2 mi · 10 min · South Skokie Highway
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17
Take the exit slight right toward IL 120 East
1323 ft · 36 sec
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18
Turn straight onto Belvidere Road
1830 ft · 33 sec · Belvidere Road
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19
Continue on Belvidere Street
1.6 mi · 3 min · Belvidere Street
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20
Turn left onto Glen Rock Avenue
2495 ft · 1 min · Glen Rock Avenue
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21
Turn left onto South Jackson Street
2647 ft · 1 min · South Jackson Street
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22
Arrive at your destination
0 m · 1 sec · North Jackson Street
Car Route Details
A richer read on the saved driving route between Sleepy Hollow and Waukegan.
Long-distance drive
This route is long enough that fuel, rest stops, weather, and timing matter more than any single maneuver.
I 57 North
Keep slight left to continue on I 57 North: Chicago
195 mi · 03h 34m
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.
Sunny leaving Sleepy Hollow and Mostly Sunny near Waukegan.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Sleepy Hollow to Waukegan?
The road trip is about 373.1 miles (600.4 km) and usually takes 05h 57m 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?
Tolono is a useful midpoint, sitting about 184.6 miles from Sleepy Hollow and 188.5 miles from Waukegan.
How much longer is the road route than the straight-line distance?
The direct path is about 334.2 miles (537.9 km), while the road route adds roughly 38.9 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 5:06 AM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $49.63 one way or $99.25 round trip. Estimated CO2 is about 117 kg one way.
What should you check before leaving?
Before you leave, expect Sunny around Sleepy Hollow and Mostly Sunny near Waukegan.
Stop Ideas Near Tolono
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 Tolono.
Illinois Terminal
Rantoul
Danville, Illinois
Mattoon station
Flight Path Map
This map shows the direct air route between Sleepy Hollow and Waukegan. Straight-line distance: 334.25 mi (537.93 km).
#1 Sleepy Hollow
Village in Illinois
| Population | 3,215 |
| Coordinates | 37.6003300, -88.9492400 |
| Altitude | 163 |
| Country | United States |
#2 Waukegan
The second most populous city in Lake County, Illinois.
| Population | 85,453 |
| Coordinates | 42.3636300, -87.8447900 |
| Altitude | 199 |
| Country | United States |
End: North Jackson Street (-87.844706, 42.363629)
Estimated Travel Time
Distance: 600 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 12h 25m |
| 40 mph (64.37 km/h) | 09h 19m |
| 50 mph (80.47 km/h) | 07h 27m |
| 60 mph (96.56 km/h) | 06h 13m |
| 70 mph (112.65 km/h) | 05h 19m |
| 80 mph (129 km/h) | 04h 39m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $49.63 | $99.25 |
| Mid-grade | $4.25 | $55.97 | $111.94 |
| Premium | $4.65 | $61.25 | $122.49 |
| Diesel | $5.30 | $69.80 | $139.60 |
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 19, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.