Origin
Sleepy Hollow, IL
Late night in Sleepy Hollow on Friday
Local time
2:14 AM
CDT
Current temp
50°F
Unavailable
Live forecast
Trip from Sleepy Hollow, IL to Chicago, IL
Compiled by the Trip.ovh editorial team · Last recalculated Apr 17, 2026 · Methodology
Drive Time
1h 5m
Distance
44.1 mi
71 km
Drive Score
7/10
Good drive
Same Day?
Yes, doable
Fuel Cost
$7
one way
EV Charging
Unknown
Best Time to Leave
4 AM
1h 0m
★
6 AM
1h 5m
8 AM
1h 16m
10 AM
1h 9m
12 PM
1h 8m
3 PM
1h 10m
5 PM
1h 15m
8 PM
1h 2m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Sleepy Hollow, IL
Stéphane Tendon
Chicago, IL
Otoniel Alvarado
Trip Overview
The drive from Sleepy Hollow, IL to Chicago, IL covers 44.1 miles and takes about 1h 5m 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 Avenue for much of the mileage, and the overall profile is turn-heavy local drive. The longest uninterrupted segment is about 24 miles on Jane Addams Memorial Tollway. At current regular gas prices, budget about $6.89 one way before food or hotel costs.
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 1h 5m. Total distance: 44.1 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 5m 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 5m drive with frequent turns across 44.1 miles of local and secondary roads.
This route has more turning and local-road decision points than a simple highway run.
There are about 33 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 24 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 0.3 miles in near Locust Drive.
Driving Effort
10/10
Demanding - stay alert through the decision-heavy sections
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 44.1 miles you will encounter 26 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 0.3 miles (Locust Drive): Complex interchange - multiple decisions in a short stretch; at 26.3 miles (I 90 / Jane Addams Memorial Tollway): Highway fork - watch signs carefully. Lane positioning matters here; at 26.8 miles (Cumberland flyover): Exit ramp - move to the correct lane early. Lane positioning matters here.
Critical Maneuvers
5 of 26 key pointsThese are the spots where you need to pay the most attention. Preview them before you drive.
6
0.3 mi into trip
|
~1m in
|
Locust Drive
At end of road, turn right onto Locust Drive
Complex interchange - multiple decisions in a short stretch
7
26.3 mi into trip
|
~32m in
|
I 90 / Jane Addams Memorial Tollway
Keep slight right at fork onto I 90 / Jane Addams Memorial Tollway toward Cumberland Avenue
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
Toward Cumberland Avenue
7
26.8 mi into trip
|
~33m in
|
Cumberland flyover
Take the exit onto Cumberland flyover toward IL 171 South: Cumberland Avenue South
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the straight / slight right lanes.
Exit 79A
Toward IL 171 South: Cumberland Avenue South
6
27.9 mi into trip
|
~35m in
|
IL 171 / North Cumberland Avenue
Turn right onto IL 171 / North Cumberland Avenue
Lane positioning matters here
Use the right lane.
7
43.1 mi into trip
|
~1h 2m in
Take the exit toward 18th Street
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the slight right lane.
Exit 52C
Toward 18th Street
Main Roads
| Road | Distance | Duration |
|---|---|---|
| Jane Addams Memorial Tollway | 24 mi | 26m |
| Kennedy Expressway | 7.9 mi | 11m |
| West Higgins Avenue | 2.7 mi | 6m |
| South 8th Street | 1.2 mi | 2m |
| West Higgins Road | 1.1 mi | 1m |
| Cumberland flyover | 1 mi | 1m |
| Dan Ryan Expressway | 0.9 mi | 1m |
| Willow Lane | 0.8 mi | 3m |
Longest stretch:
Jane Addams Memorial Tollway
— 24 mi, about 26m
Turn-by-Turn Driving Directions
Step-by-step road directions between Sleepy Hollow, IL and Chicago, IL.
1
Start on Willow Lane
0.3 mi
·
1 min
·
Willow Lane
2
At end of road, turn right onto Locust Drive
435 ft
·
24 sec
·
Locust Drive
3
Turn left onto Willow Lane
0.4 mi
·
1 min
·
Willow Lane
4
Continue on Willow Lane
279 ft
·
16 sec
·
Willow Lane
5
Turn right onto IL 31
1.2 mi
·
2 min
·
South 8th Street
6
Continue on IL 31
0.5 mi
·
54 sec
·
North State Street
7
Take the ramp
0.3 mi
·
1 min
Toward I 90 East Toll: Chicago
Use the right lane.
8
Merge onto I 90
23 mi
·
25 min
·
Jane Addams Memorial Tollway
Use the straight / slight right lanes.
9
Keep slight right at fork onto I 90
0.3 mi
·
21 sec
·
Jane Addams Memorial Tollway
Toward Cumberland Avenue
Use the straight / slight right lanes.
10
Keep slight left at fork onto I 90
526 ft
·
29 sec
·
Jane Addams Memorial Tollway
11
Merge onto I 90
402 ft
·
4 sec
·
Jane Addams Memorial Tollway
12
Take the exit onto Cumberland flyover
1.0 mi
·
1 min
·
Cumberland flyover
Exit 79A
Toward IL 171 South: Cumberland Avenue South
Use the straight / slight right lanes.
13
Keep slight left at fork
245 ft
·
8 sec
Toward IL 171 South: Cumberland Avenue
14
Turn right onto IL 171
0.2 mi
·
28 sec
·
North Cumberland Avenue
Use the right lane.
15
Continue on IL 171
0.4 mi
·
1 min
·
North Cumberland Avenue
Use the left lane.
16
Turn right onto IL 72
1.1 mi
·
1 min
·
West Higgins Road
17
Turn right onto IL 72
326 ft
·
13 sec
·
North Oriole Avenue
Use the left / right lanes.
18
Turn left onto IL 72
2.7 mi
·
6 min
·
West Higgins Avenue
19
Turn right onto North Central Avenue
0.2 mi
·
25 sec
·
North Central Avenue
20
Turn left onto West Lawrence Avenue
0.4 mi
·
42 sec
·
West Lawrence Avenue
Use the left lane.
21
Turn right onto North Milwaukee Avenue
0.6 mi
·
1 min
·
North Milwaukee Avenue
22
Turn left onto West Montrose Avenue
0.5 mi
·
1 min
·
West Montrose Avenue
23
Take the ramp
0.3 mi
·
42 sec
Toward I 90 East, I 94 East
24
Merge onto I 90; I 94
7.9 mi
·
11 min
·
Kennedy Expressway
Use the straight / slight left lanes.
25
Continue on I 90; I 94
0.9 mi
·
1 min
·
Dan Ryan Expressway
26
Take the exit
0.3 mi
·
34 sec
Exit 52C
Toward 18th Street
Use the slight right lane.
27
Turn slight left onto South Union Avenue
0.2 mi
·
30 sec
·
South Union Avenue
28
Turn right onto South Canalport Avenue
505 ft
·
12 sec
·
South Canalport Avenue
29
Turn left onto South Halsted Street
0.1 mi
·
18 sec
·
South Halsted Street
30
Turn right onto West Cermak Road
0.2 mi
·
24 sec
·
West Cermak Road
31
Turn left
152 ft
·
11 sec
32
Turn right
0.2 mi
·
58 sec
33
Arrive at destination
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 22.1 mi from Sleepy Hollow, IL · 28m into the drive
Mid-route town
Meal stop
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
Fuel and coffee
A short stop after about 10 miles helps settle the day before fatigue starts building.
Meal break
The midpoint is around 22.1 miles from Sleepy Hollow, IL, which is a good place for a longer meal and fuel stop.
Arriving in Chicago, IL
The final approach into Chicago, 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
$6.89 one way
$13.79 round trip
$3.97/gal
25.4 MPG avg
15 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.36 | $7.57 | $15.14 |
| premium | $4.89 | $8.49 | $16.97 |
| diesel | $5.61 | $9.74 | $19.47 |
Estimated Tolls: $1.64
Jane Addams Memorial Tollway
(23.5 mi)
$1.64
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
$9
Estimated CO2 emission: 15.4 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 | 13.2 | 0 | $4.63 | $2.12 |
| Efficient EV | 11 | 0 | $3.86 | $1.76 |
| EV Truck/SUV | 17.6 | 0 | $6.17 | $2.82 |
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.
Destination
Chicago, IL
Late night in Chicago on Friday
Local time
2:14 AM
CDT
Current temp
43°F
Widespread Fog
ESE 0 to 5 mph
0% chance
Live forecast
Dense Fog Advisory
Dense Fog Advisory issued April 16 at 11:52PM CDT until April 17 at 10:00AM CDT by NWS Chicago IL
Dense Fog Advisory
Dense Fog Advisory issued April 16 at 11:52PM CDT until April 17 at 10:00AM CDT by NWS Chicago IL
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
7 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 5m 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 Sleepy Hollow, IL to Chicago, IL covers 44.1 miles and takes about 1h 5m 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 Avenue. Expect a mix of highway and local road driving.
This is a comfortable same-day trip.
The midpoint is about 22.1 miles from Sleepy Hollow, IL. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $6.89 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 44.1 miles you will encounter 26 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 0.3 miles (Locust Drive): Complex interchange - multiple decisions in a short stretch; at 26.3 miles (I 90 / Jane Addams Memorial Tollway): Highway fork - watch signs carefully. Lane positioning matters here; at 26.8 miles (Cumberland flyover): Exit ramp - move to the correct lane early. Lane positioning matters here.
The route from Sleepy Hollow, IL to Chicago, IL does not surface many named destination signs beyond the main corridor.
Yes. Nearby national parks include Pullman National Historical Park.
Data sources
The figures on this page are computed from open government and mapping datasets, not crowdsourced reviews. Distances and geometry come from OSRM over OpenStreetMap. Fuel cost uses EIA weekly regional averages. National park proximity is from the NPS API. Full methodology, refresh cadence, and limitations are documented on the methodology page.
Was this helpful?
Thanks for your feedback!
Your tip has been submitted. Thanks!
/500
Recent Tips
·
Explore More
Continue From Chicago, IL
More from Sleepy Hollow, IL
More trips to Chicago, IL
Explore more options from Sleepy Hollow, IL or browse trips ending in Chicago, IL.
Looking for more statewide routes? Browse IL road trips.