How far is Chicago, IL from Sleepy Hollow, IL?
The driving distance from Chicago, IL to Sleepy Hollow, IL is about 328.1 miles (528 km), with a travel time of about 06h 07m by car.
- The straight-line flight distance is about 301.6 miles (485.4 km).
- For a round trip, plan for roughly 12h 15m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 7:30 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 06h 07m.
Starting early still helps, but most travelers will want a longer stop or an overnight stay on a route this long.
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.
Township in Douglas County, Illinois
Route Weather Snapshot
Check the forecast at both ends before you head out.
Slight Chance Snow Showers then Mostly Sunny
Sunny
Driving Route Map
The map below follows the saved road route between Chicago and Sleepy Hollow.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chicago and Sleepy Hollow.
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1
Start on the route
943 ft · 1 min
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2
At the end of the road, turn right onto West Cermak Road
947 ft · 26 sec · West Cermak Road
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3
Turn left onto South Halsted Street
737 ft · 17 sec · South Halsted Street
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4
Turn right onto South Canalport Avenue
87 m · 6 sec · South Canalport Avenue
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5
Turn slight right
34 m · 5 sec
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6
Take the ramp straight toward I 90 East, I 94 East
139 m · 11 sec
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7
Keep slight left to continue on I 90, I 94 East: Indiana
929 ft · 23 sec
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8
Merge slight left onto Dan Ryan Expressway
1.2 km · 48 sec · Dan Ryan Expressway
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9
Keep slight left to continue on Dan Ryan Expressway (Express)
8.8 mi · 12 min · Dan Ryan Expressway (Express)
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10
Keep slight right to continue on I 57 South: Memphis
200.8 mi · 3 hr 41 min
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11
Keep slight left to continue on I 57 South: Memphis
65.7 mi · 1 hr 11 min
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12
Keep slight right to continue on Ken Gray Expressway
46.8 mi · 50 min · Ken Gray Expressway
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13
Take the exit slight right toward IL 148
1415 ft · 50 sec
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14
Turn right
1.1 km · 1 min
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15
Turn left
1753 ft · 31 sec
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16
Turn right onto Lake Egypt Road
1.5 km · 2 min · Lake Egypt Road
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17
Turn right onto Power Plant Road
2.1 mi · 5 min · Power Plant Road
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18
Turn left onto Sleepy Hollow Lane
145 m · 21 sec · Sleepy Hollow Lane
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19
Arrive at your destination
0 m · 1 sec · Sleepy Hollow Lane
Car Route Details
A richer read on the saved driving route between Chicago and Sleepy Hollow.
Long-distance drive
This route is long enough that fuel, rest stops, weather, and timing matter more than any single maneuver.
I 57 South
Keep slight right to continue on I 57 South: Memphis
201 mi · 03h 41m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
Better with a longer stop
This route is long enough that most travelers will be better off planning an overnight stay or a more deliberate stop window.
Slight Chance Snow Showers then Mostly Sunny leaving Chicago and Sunny near Sleepy Hollow.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chicago to Sleepy Hollow?
The road trip is about 328.1 miles (528 km) and usually takes 06h 07m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route is long enough that most travelers will be better off planning an overnight stay or a more deliberate stop window.
What is the halfway point on this route?
Arcola is a useful midpoint, sitting about 164.2 miles from Chicago and 163.9 miles from Sleepy Hollow.
How much longer is the road route than the straight-line distance?
The direct path is about 301.6 miles (485.4 km), while the road route adds roughly 26.5 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 7:30 AM CDT. Starting early still helps, but most travelers will want a longer stop or an overnight stay on a route this long.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $43.67 one way or $87.34 round trip. Estimated CO2 is about 102.9 kg one way.
What should you check before leaving?
Before you leave, expect Slight Chance Snow Showers then Mostly Sunny around Chicago and Sunny near Sleepy Hollow.
Stop Ideas Near Arcola
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 Arcola.
Mattoon station
Illinois Terminal
Effingham
Rantoul
Flight Path Map
This map shows the direct air route between Chicago and Sleepy Hollow. Straight-line distance: 301.62 mi (485.41 km).
#1 Chicago
The third most populous city in the United States and the center of the Chicago metropolitan area.
| Population | 2,677,643 |
| Coordinates | 41.850033, -87.6500523 |
| Altitude | 179 |
| Country | United States |
#2 Sleepy Hollow
Village in Illinois
| Population | 3,215 |
| Coordinates | 37.6003300, -88.9492400 |
| Altitude | 163 |
| Country | United States |
End: Sleepy Hollow (-88.94924, 37.60033)
Estimated Travel Time
Distance: 528 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 10h 55m |
| 40 mph (64.37 km/h) | 08h 12m |
| 50 mph (80.47 km/h) | 06h 33m |
| 60 mph (96.56 km/h) | 05h 28m |
| 70 mph (112.65 km/h) | 04h 41m |
| 80 mph (129 km/h) | 04h 05m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $43.67 | $87.34 |
| Mid-grade | $4.25 | $49.25 | $98.50 |
| Premium | $4.65 | $53.89 | $107.79 |
| Diesel | $5.30 | $61.42 | $122.84 |
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.