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Trip from Chicago, IL to Sleepy Hollow, IL

Compiled and reviewed by the Trip.ovh planning team at COD Solutions Oy · Last reviewed Apr 17, 2026 · Editorial standards

Drive Time

1h 3m

Distance

43 mi

69 km

Drive Score

7/10

Good drive

Same Day?

Yes, doable

Fuel Cost

$7

one way

EV Charging

Unknown

Best Time to Leave

Save up to 16 min
4 AM
0h 58m ★
6 AM
1h 3m
8 AM
1h 14m
10 AM
1h 7m
12 PM
1h 6m
3 PM
1h 7m
5 PM
1h 13m
8 PM
1h 0m

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 chicago-il

Chicago, IL

Otoniel Alvarado

Downtown Sleepy Hollow, IL, IL

Sleepy Hollow, IL

Stéphane Tendon

Trip Overview

The drive from Chicago, IL to Sleepy Hollow, IL covers 43 miles and takes about 1h 3m behind the wheel. This route is realistic as a one-day drive if you keep your stops efficient.

The route leans on Jane Addams Memorial Tollway, Kennedy Expressway, West Higgins Road for much of the mileage, and the overall profile is turn-heavy local drive. The longest uninterrupted segment is about 22.2 miles on Jane Addams Memorial Tollway. At current regular gas prices, budget about $6.72 one way before food or hotel costs.

Who Is This Route For?

Weekend Trip

Doable as a same-day drive at 1h 3m. Total distance: 43 miles.

Family Friendly

Moderate complexity with 0 natural rest stops along the way.

Solo Traveler

1h 3m drive, comfortable solo distance.

EV Driver

0 DC fast chargers along the route. Coverage: unknown.

Scenic Drive

Turn-heavy local drive route profile with national parks nearby.

Drive Character

Expect a 1h 3m drive with frequent turns across 43 miles of local and secondary roads.

This route has more turning and local-road decision points than a simple highway run.
There are about 24 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
Jane Addams Memorial Tollway is the longest continuous segment at about 22.2 miles.

How Hard Is This Drive?

Expect a hands-on drive with frequent turns and local roads rather than long highway stretches. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 0.2 miles in near West Cermak Road.

Driving Effort 7/10

Demanding - plan breaks and stay ahead of the key maneuvers

Balances navigation complexity with total wheel time.

This drive requires moderate attention. Across 43 miles you will encounter 17 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.

Where does it get tricky?

The main spots that need attention: at 0.2 miles (West Cermak Road): Navigation decision point; at 0.4 miles (South Halsted Street): Lane positioning matters here; at 0.7 miles (South Ruble Street): Lane positioning matters here.

Critical Maneuvers

5 of 17 key points

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

5
0.2 mi into trip | ~1m in | West Cermak Road

At end of road, turn right onto West Cermak Road

Navigation decision point

6
0.4 mi into trip | ~1m in | South Halsted Street

Turn left onto South Halsted Street

Lane positioning matters here

Use the left lane.
6
0.7 mi into trip | ~2m in | South Ruble Street

Turn left onto South Ruble Street

Lane positioning matters here

Use the left lane.
7
9.9 mi into trip | ~16m in

Take the exit toward Montrose Avenue

Exit ramp - move to the correct lane early. Lane positioning matters here

Use the slight right lane. Exit 43C Toward Montrose Avenue
7
40.3 mi into trip | ~56m in

Take the exit toward IL 31 North

Exit ramp - move to the correct lane early. Lane positioning matters here

Use the straight / slight right lanes. Exit 54B Toward IL 31 North

Main Roads

Road Distance Duration
Jane Addams Memorial Tollway 22.2 mi 23m
Kennedy Expressway 7.9 mi 11m
West Higgins Road 3.1 mi 5m
West Bryn Mawr Avenue 1.8 mi 4m
South 8th Street 1.2 mi 2m
North Milwaukee Avenue 1.1 mi 2m
North Northwest Highway 1 mi 1m
Dan Ryan Expressway 0.9 mi 1m
Longest stretch: Jane Addams Memorial Tollway — 22.2 mi, about 23m

Turn-by-Turn Driving Directions

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

1

Start on this road

0.2 mi · 1 min · this road
2

At end of road, turn right onto West Cermak Road

0.2 mi · 26 sec · West Cermak Road
3

Turn left onto South Halsted Street

0.1 mi · 17 sec · South Halsted Street
Use the left lane.
4

Turn right onto South Canalport Avenue

0.2 mi · 22 sec · South Canalport Avenue
5

Turn left onto South Ruble Street

0.1 mi · 22 sec · South Ruble Street
Use the left lane.
6

Take the ramp

0.3 mi · 43 sec
Toward I 90 West, I 94 West
7

Merge onto I 90; I 94

0.9 mi · 1 min · Dan Ryan Expressway
Use the straight / slight right lanes.
8

Continue on I 90; I 94

7.9 mi · 11 min · Kennedy Expressway
Use the straight / slight right lanes.
9

Take the exit

0.2 mi · 28 sec
Exit 43C Toward Montrose Avenue Use the slight right lane.
10

Turn left onto West Montrose Avenue

0.7 mi · 1 min · West Montrose Avenue
11

Turn right onto North Milwaukee Avenue

1.1 mi · 2 min · North Milwaukee Avenue
12

Turn left onto North Northwest Highway

67 ft · 1 sec · North Northwest Highway
13

Continue on North Northwest Highway

1.0 mi · 1 min · North Northwest Highway
14

Turn slight left onto West Bryn Mawr Avenue

1.8 mi · 4 min · West Bryn Mawr Avenue
Use the left lane.
15

Continue on IL 72

3.1 mi · 5 min · West Higgins Road
Use the straight / left / right lanes.
16

Take the ramp

0.3 mi · 32 sec
Toward I 90 Toll West
17

Merge onto I 90

22 mi · 23 min · Jane Addams Memorial Tollway
Use the straight / slight right lanes.
18

Take the exit

0.4 mi · 42 sec
Exit 54B Toward IL 31 North Use the straight / slight right lanes.
19

Turn straight onto IL 31

0.2 mi · 24 sec · North State Street
20

Continue on IL 31

1.2 mi · 2 min · South 8th Street
Use the left lane.
21

Turn left onto Willow Lane

0.5 mi · 1 min · Willow Lane
22

At end of road, turn right onto Locust Drive

435 ft · 24 sec · Locust Drive
23

Turn left onto Willow Lane

0.3 mi · 1 min · Willow Lane
24

Arrive at destination

Willow Lane

Where to Stop

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

Halfway Point

Midpoint

About 21.5 mi from Chicago, IL · 36m into the drive

village in Cook County, Illinois, United States

Mid-route town

Meal stop

Schiller Park, IL

22 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.

Pacing Suggestions

East Dundee, IL

Fuel and coffee

A short stop after about 43 miles helps settle the day before fatigue starts building.

Des Plaines, IL

Meal break

The midpoint is around 21.5 miles from Chicago, IL, which is a good place for a longer meal and fuel stop.

Arriving in Sleepy Hollow, IL

The final approach into Sleepy Hollow, IL usually feels slower than the middle of the drive, so avoid planning your tightest schedule at the very end.

These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.

Fuel & Cost

Regular Gas

$6.72 one way

$13.45 round trip

$3.97/gal 25.4 MPG avg 15 kg CO2
Fuel Type $/gal One Way Round Trip
midgrade $4.36 $7.38 $14.76
premium $4.89 $8.27 $16.55
diesel $5.61 $9.49 $18.99

Estimated Tolls: $1.56

Jane Addams Memorial Tollway (22.2 mi) $1.56

Toll estimates based on average 2024-2025 rates. EZ-Pass/SunPass discounts may lower the actual cost.

Drive Cost (one way)

Fuel

$7

Tolls

$2

Total

$8

Estimated CO2 emission: 15 kg one way. Prices: EIA weekly data, 2026-04-13.

Driving Electric?

About $5 in charging · 0 stops · 67% less CO2

Vehicle Type kWh Stops DC Fast Home Charge
Average EV 12.9 0 $4.52 $2.06
Efficient EV 10.8 0 $3.76 $1.72
EV Truck/SUV 17.2 0 $6.02 $2.75

Gas CO2

15 kg

EV CO2

5 kg (67% less)

This trip is well within single-charge range for most EVs. No charging stops needed if you start fully charged.

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 as of Apr 16, 2026

Origin

Chicago, IL

Afternoon in Chicago on Friday

Local time

1:56 PM

CDT

Current temp

68°F

Scattered Showers And Thunderstorms

NNW 10 to 15 mph 41% chance Live forecast

Flood Warning

Flood Warning issued April 16 at 12:33PM CDT until April 18 at 7:00PM CDT by NWS Chicago IL

Flood Watch

Flood Watch issued April 16 at 12:29PM CDT by NWS Chicago IL

Destination

Sleepy Hollow, IL

Afternoon in Sleepy Hollow on Friday

Local time

1:56 PM

CDT

Current temp

50°F

Unavailable

Live forecast

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

18 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

1h 3m on the road

The weather snapshot is not static. If you are leaving later, give both cities one more quick forecast check before departure.

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

Frequently Asked Questions

The drive from Chicago, IL to Sleepy Hollow, IL covers 43 miles and takes about 1h 3m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.

The main roads are Jane Addams Memorial Tollway, Kennedy Expressway, West Higgins Road. Expect a mix of highway and local road driving.

This is a comfortable same-day trip.

The midpoint is about 21.5 miles from Chicago, IL. Look for rest areas, gas stations, or food options near the halfway mark.

At current regular gas prices, expect to spend about $6.72 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.

Leave by 9 AM and you'll arrive before lunch. Even a 4 PM departure gets you there before dark in summer.

This drive requires moderate attention. Across 43 miles you will encounter 17 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.

The main spots that need attention: at 0.2 miles (West Cermak Road): Navigation decision point; at 0.4 miles (South Halsted Street): Lane positioning matters here; at 0.7 miles (South Ruble Street): Lane positioning matters here.

The route from Chicago, IL to Sleepy Hollow, IL does not surface many named destination signs beyond the main corridor.

Yes. Nearby national parks include Pullman National Historical Park.

How this page is built

Compiled by the Trip.ovh planning team at COD Solutions Oy from open government datasets — OSRM over OpenStreetMap for geometry, EIA for fuel prices, and NPS for national parks. See our methodology for refresh cadence and limitations.

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