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Trip from Evanston, 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

55m

Distance

37.2 mi

60 km

Drive Score

6/10

Good drive

Same Day?

Yes, doable

Fuel Cost

$6

one way

EV Charging

Unknown

Best Time to Leave

Save up to 13 min
4 AM
0h 51m ★
6 AM
0h 55m
8 AM
1h 4m
10 AM
0h 58m
12 PM
0h 57m
3 PM
0h 59m
5 PM
1h 4m
8 PM
0h 52m

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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suburban city in Cook County, Illinois, United States

Evanston, IL

Wikimedia Commons

Downtown Sleepy Hollow, IL, IL

Sleepy Hollow, IL

Stéphane Tendon

Trip Overview

The drive from Evanston, IL to Sleepy Hollow, IL covers 37.2 miles and takes about 55m 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, Oakton Street, West Touhy Avenue 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 $5.82 one way before food or hotel costs.

Who Is This Route For?

Weekend Trip

Doable as a same-day drive at 55m. Total distance: 37.2 miles.

Family Friendly

Moderate complexity with 0 natural rest stops along the way.

Solo Traveler

55m 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 55m drive with frequent turns across 37.2 miles of local and secondary roads.

This route has more turning and local-road decision points than a simple highway run.
There are about 22 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. You will hit about 15 points where you need to pay attention to lane position or signs. The trickiest moment comes early in the drive.

Driving Effort 6/10

Moderate - straightforward overall, but long enough or busy enough to require pacing

Balances navigation complexity with total wheel time.

This drive requires moderate attention. Across 37.2 miles you will encounter 15 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: near the start: Complex interchange - multiple decisions in a short stretch; at 0.1 miles (Dempster Street): Navigation decision point; at 0.1 miles (Asbury Avenue): Lane positioning matters here.

Critical Maneuvers

5 of 15 key points

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

6
0 mi into trip | ~0m in

At end of road, turn left

Complex interchange - multiple decisions in a short stretch

5
0.1 mi into trip | ~0m in | Dempster Street

At end of road, turn left onto Dempster Street

Navigation decision point

6
0.1 mi into trip | ~0m in | Asbury Avenue

Turn left onto Asbury Avenue

Lane positioning matters here

Use the left lane.
6
11.1 mi into trip | ~21m in | Devon Avenue

Turn right onto Devon Avenue

Lane positioning matters here

Use the left lane.
7
34.5 mi into trip | ~48m 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
Oakton Street 4 mi 7m
West Touhy Avenue 3.3 mi 6m
South 8th Street 1.2 mi 2m
Asbury Avenue 1 mi 1m
South Dee Road 1 mi 2m
Devon Avenue 0.9 mi 1m
West Gross Point Road 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 Evanston, IL and Sleepy Hollow, IL.

1

Start on this road

197 ft · 21 sec · this road
2

At end of road, turn left

139 ft · 15 sec
3

At end of road, turn left onto Dempster Street

213 ft · 14 sec · Dempster Street
4

Turn left onto Asbury Avenue

1.0 mi · 1 min · Asbury Avenue
Use the left lane.
5

Turn right onto Oakton Street

4.0 mi · 7 min · Oakton Street
6

Turn slight left onto Gross Point Road

0.5 mi · 52 sec · Gross Point Road
7

Turn straight onto New Gross Point Road

0.1 mi · 14 sec · New Gross Point Road
8

Turn right onto Howard Street

0.2 mi · 34 sec · Howard Street
9

Turn left onto North Lehigh Avenue

120 ft · 2 sec · North Lehigh Avenue
10

Turn right onto West Gross Point Road

0.9 mi · 1 min · West Gross Point Road
11

Turn slight right onto West Touhy Avenue

3.3 mi · 6 min · West Touhy Avenue
Use the right lane.
12

Turn left onto South Dee Road

1.0 mi · 2 min · South Dee Road
Use the left lane.
13

Turn right onto Devon Avenue

0.9 mi · 1 min · Devon Avenue
Use the left lane.
14

Take the ramp

0.3 mi · 32 sec
Toward I 90 West Toll Use the right lane.
15

Merge onto I 90

22 mi · 23 min · Jane Addams Memorial Tollway
Use the straight / slight right lanes.
16

Take the exit

0.4 mi · 42 sec
Exit 54B Toward IL 31 North Use the straight / slight right lanes.
17

Turn straight onto IL 31

0.2 mi · 24 sec · North State Street
18

Continue on IL 31

1.2 mi · 2 min · South 8th Street
Use the left lane.
19

Turn left onto Willow Lane

0.5 mi · 1 min · Willow Lane
20

At end of road, turn right onto Locust Drive

435 ft · 24 sec · Locust Drive
21

Turn left onto Willow Lane

0.3 mi · 1 min · Willow Lane
22

Arrive at destination

Willow Lane

Where to Stop

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

Halfway Point

Midpoint

About 18.6 mi from Evanston, IL · 31m into the drive

city in Cook County, Illinois, United States

Mid-route town

Meal stop

Des Plaines, IL

19 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 37 miles helps settle the day before fatigue starts building.

Des Plaines, IL

Meal break

The midpoint is around 18.6 miles from Evanston, IL, which is a good place for a longer meal and fuel stop.

Arriving in Sleepy Hollow, IL

Allow a few extra minutes for the final approach into Sleepy Hollow, IL if you are unfamiliar with the area.

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

Fuel & Cost

Regular Gas

$5.82 one way

$11.63 round trip

$3.97/gal 25.4 MPG avg 13 kg CO2
Fuel Type $/gal One Way Round Trip
midgrade $4.36 $6.39 $12.77
premium $4.89 $7.16 $14.32
diesel $5.61 $8.21 $16.43

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

$6

Tolls

$2

Total

$7

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

Driving Electric?

About $4 in charging · 0 stops · 69% less CO2

Vehicle Type kWh Stops DC Fast Home Charge
Average EV 11.2 0 $3.91 $1.79
Efficient EV 9.3 0 $3.26 $1.49
EV Truck/SUV 14.9 0 $5.21 $2.38

Gas CO2

13 kg

EV CO2

4 kg (69% 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

Evanston, IL

Afternoon in Evanston on Friday

Local time

1:22 PM

CDT

Current temp

67°F

Scattered Showers And Thunderstorms

NNW 10 to 15 mph 42% 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

1:22 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

17 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

55m 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 Evanston, IL to Sleepy Hollow, IL covers 37.2 miles and takes about 55m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.

The main roads are Jane Addams Memorial Tollway, Oakton Street, West Touhy Avenue. Expect a mix of highway and local road driving.

This is a comfortable same-day trip.

The midpoint is about 18.6 miles from Evanston, IL. Look for rest areas, gas stations, or food options near the halfway mark.

At current regular gas prices, expect to spend about $5.82 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 37.2 miles you will encounter 15 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: near the start: Complex interchange - multiple decisions in a short stretch; at 0.1 miles (Dempster Street): Navigation decision point; at 0.1 miles (Asbury Avenue): Lane positioning matters here.

The route from Evanston, 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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