How far is Chicago, IL from Sleepy Hollow, IL?
The driving distance from Chicago, IL to Sleepy Hollow, IL is about 43 miles (69.2 km), with a travel time of about 01h 03m by car.
- The straight-line flight distance is about 37.5 miles (60.4 km).
- For a round trip, plan for roughly 02h 06m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 8:00 AM to 10:00 AM CST.
Reverse, save, or send this route
This route works well as a day trip with time at the destination. Copy the route link, send it to another device, or print a clean version before you head out.
This route works well as a day trip with time at the destination.
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 01h 03m.
A morning start gives you useful time at the destination and keeps the return out of the late evening.
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 Cook County, Illinois
Route Weather Snapshot
Check the forecast at both ends before you head out.
Partly Sunny
Mostly 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
881 ft · 23 sec · South Canalport Avenue
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5
Turn left onto South Ruble Street
676 ft · 23 sec · South Ruble Street
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6
Take the ramp straight toward I 90 West, I 94 West
1758 ft · 43 sec
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7
Merge slight left onto Dan Ryan Expressway
1.5 km · 1 min · Dan Ryan Expressway
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8
Continue on Kennedy Expressway
7.9 mi · 11 min · Kennedy Expressway
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9
Take the exit slight right toward Montrose Avenue
1041 ft · 29 sec
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10
Turn left onto West Montrose Avenue
1.1 km · 1 min · West Montrose Avenue
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11
Turn right onto North Milwaukee Avenue
1.1 mi · 2 min · North Milwaukee Avenue
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12
Turn left onto North Northwest Highway
21 m · 2 sec · North Northwest Highway
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13
Continue on North Northwest Highway
1.6 km · 2 min · North Northwest Highway
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14
Turn slight left onto West Bryn Mawr Avenue
1.8 mi · 4 min · West Bryn Mawr Avenue
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15
Continue on West Higgins Road
3.1 mi · 5 min · West Higgins Road
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16
Take the ramp right toward I 90 Toll West
1334 ft · 33 sec
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17
Merge slight left onto Jane Addams Memorial Tollway
22.2 mi · 24 min · Jane Addams Memorial Tollway
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18
Take the exit slight right toward IL 31 North
2245 ft · 43 sec
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19
Turn straight onto North State Street
1175 ft · 24 sec · North State Street
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20
Continue on South 8th Street
1.2 mi · 2 min · South 8th Street
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21
Turn left onto Willow Lane
2559 ft · 2 min · Willow Lane
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22
At the end of the road, turn right onto Locust Drive
133 m · 25 sec · Locust Drive
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23
Turn left onto Willow Lane
1607 ft · 1 min · Willow Lane
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24
Arrive at your destination
0 m · 1 sec · Willow Lane
Car Route Details
A richer read on the saved driving route between Chicago and Sleepy Hollow.
Turn-heavy local drive
The route has frequent decision points for its length, so lane choice and turn timing will matter more than cruising speed.
Jane Addams Memorial Tollway
Merge slight left onto Jane Addams Memorial Tollway
22.2 mi · 00h 24m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A comfortable day-trip route
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
Partly Sunny leaving Chicago and Mostly 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 43 miles (69.2 km) and usually takes 01h 03m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
What is the halfway point on this route?
Elk Grove is a useful midpoint, sitting about 21.5 miles from Chicago and 21.6 miles from Sleepy Hollow.
How much longer is the road route than the straight-line distance?
The direct path is about 37.5 miles (60.4 km), while the road route adds roughly 5.5 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 8:00 AM to 10:00 AM CST. If you want a more comfortable same-day return, try to leave by 4:24 PM CST.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $6.83 one way or $13.66 round trip. Estimated CO2 is about 13.5 kg one way.
What should you check before leaving?
Before you leave, expect Partly Sunny around Chicago and Mostly Sunny near Sleepy Hollow.
Stop Ideas Near Elk Grove
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 Elk Grove.
Glenview station
La Grange Road
Summit
Chicago Union Station
Flight Path Map
This map shows the direct air route between Chicago and Sleepy Hollow. Straight-line distance: 37.52 mi (60.39 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
Sleepy Hollow is a place in Illinois, United States.
| Population | 0 |
| Coordinates | 42.0941900, -88.3025800 |
| Altitude | 225 |
| Country | United States |
End: Sleepy Hollow (-88.30258, 42.09419)
Estimated Travel Time
Distance: 69 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 01h 26m |
| 40 mph (64.37 km/h) | 01h 04m |
| 50 mph (80.47 km/h) | 00h 51m |
| 60 mph (96.56 km/h) | 00h 43m |
| 70 mph (112.65 km/h) | 00h 36m |
| 80 mph (129 km/h) | 00h 32m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.50 | $6.83 | $13.66 |
| Mid-grade | $5.12 | $7.78 | $15.56 |
| Premium | $5.68 | $8.63 | $17.26 |
| Diesel | $6.52 | $9.91 | $19.82 |
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 · Nov 09, 2026