How far is Sleepy Hollow, IL from Chicago, IL?
The driving distance from Sleepy Hollow, IL to Chicago, IL is about 43.3 miles (69.7 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.
Mostly Sunny
Mostly Sunny
Driving Route Map
The map below follows the saved road route between Sleepy Hollow and Chicago.
Turn-by-Turn Driving Directions
Step-by-step road directions between Sleepy Hollow and Chicago.
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1
Start on Willow Lane
1607 ft · 1 min · Willow Lane
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2
At the end of the road, turn right onto Locust Drive
133 m · 24 sec · Locust Drive
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3
Turn left onto Willow Lane
2242 ft · 2 min · Willow Lane
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4
Continue on Willow Lane
85 m · 16 sec · Willow Lane
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5
Turn right onto South 8th Street
1.2 mi · 2 min · South 8th Street
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6
Continue on North State Street
2766 ft · 54 sec · North State Street
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7
Take the ramp slight right toward I 90 East Toll: Chicago
1404 ft · 1 min
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8
Merge slight left onto Jane Addams Memorial Tollway
23.5 mi · 25 min · Jane Addams Memorial Tollway
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9
Keep slight right to continue on Jane Addams Memorial Tollway
1772 ft · 22 sec · Jane Addams Memorial Tollway
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10
Keep slight left to continue on Jane Addams Memorial Tollway
526 ft · 30 sec · Jane Addams Memorial Tollway
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11
Merge slight right onto Jane Addams Memorial Tollway
123 m · 5 sec · Jane Addams Memorial Tollway
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12
Take the exit slight right toward IL 171 South: Cumberland Avenue South
1 mi · 2 min · Cumberland flyover
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13
Keep slight left to continue on IL 171 South: Cumberland Avenue
75 m · 8 sec
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14
Turn right onto North Cumberland Avenue
874 ft · 28 sec · North Cumberland Avenue
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15
Continue on North Cumberland Avenue
2310 ft · 1 min · North Cumberland Avenue
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16
Turn right onto West Higgins Road
1.1 mi · 2 min · West Higgins Road
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17
Turn right onto North Oriole Avenue
99 m · 14 sec · North Oriole Avenue
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18
Turn left onto West Higgins Avenue
2.7 mi · 6 min · West Higgins Avenue
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19
Turn right onto North Central Avenue
929 ft · 26 sec · North Central Avenue
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20
Turn left onto West Lawrence Avenue
1858 ft · 43 sec · West Lawrence Avenue
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21
Turn right onto North Milwaukee Avenue
3138 ft · 1 min · North Milwaukee Avenue
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22
Turn left onto West Montrose Avenue
2904 ft · 1 min · West Montrose Avenue
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23
Take the ramp slight right toward I 90 East, I 94 East
1721 ft · 42 sec
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24
Merge slight left onto Kennedy Expressway
7.9 mi · 11 min · Kennedy Expressway
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25
Continue on Dan Ryan Expressway
1.5 km · 1 min · Dan Ryan Expressway
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26
Take the exit slight right toward 18th Street
1398 ft · 34 sec
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27
Turn slight left onto South Union Avenue
963 ft · 30 sec · South Union Avenue
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28
Turn right onto South Canalport Avenue
154 m · 13 sec · South Canalport Avenue
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29
Turn left onto South Halsted Street
737 ft · 19 sec · South Halsted Street
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30
Turn right onto West Cermak Road
976 ft · 25 sec · West Cermak Road
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31
Turn left
46 m · 11 sec
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32
Turn right
794 ft · 58 sec
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33
Arrive at your destination
0 m · 1 sec
Car Route Details
A richer read on the saved driving route between Sleepy Hollow and Chicago.
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
23.5 mi · 00h 25m
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.
Mostly Sunny leaving Sleepy Hollow and Mostly Sunny near Chicago.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Sleepy Hollow to Chicago?
The road trip is about 43.3 miles (69.7 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 22 miles from Sleepy Hollow and 21.3 miles from Chicago.
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 5.8 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 $6.88 one way or $13.75 round trip. Estimated CO2 is about 13.6 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny around Sleepy Hollow and Mostly Sunny near Chicago.
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 Sleepy Hollow and Chicago. Straight-line distance: 37.52 mi (60.39 km).
#1 Sleepy Hollow
Sleepy Hollow is a place in Illinois, United States.
| Population | 0 |
| Coordinates | 42.0941900, -88.3025800 |
| Altitude | 225 |
| Country | United States |
#2 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 |
End: (-87.650099, 41.850032)
Estimated Travel Time
Distance: 70 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 37m |
| 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 | $6.88 | $13.75 |
| Mid-grade | $5.12 | $7.83 | $15.66 |
| Premium | $5.68 | $8.69 | $17.37 |
| Diesel | $6.52 | $9.98 | $19.95 |
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