How far is Winthrop Harbor, IL from Chicago, IL?
The driving distance from Winthrop Harbor, IL to Chicago, IL is about 59.5 miles (95.7 km), with a travel time of about 01h 12m by car.
- The straight-line flight distance is about 44.4 miles (71.4 km).
- For a round trip, plan for roughly 02h 24m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 8:00 AM to 10:00 AM CDT.
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 12m.
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.
City in Lake County, Illinois, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Mostly Sunny
Slight Chance Snow Showers then Mostly Sunny
Driving Route Map
The map below follows the saved road route between Winthrop Harbor and Chicago.
Turn-by-Turn Driving Directions
Step-by-step road directions between Winthrop Harbor and Chicago.
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1
Start on Sheridan Road
6.6 mi · 14 min · Sheridan Road
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2
Turn left onto West Greenwood Avenue
1637 ft · 32 sec · West Greenwood Avenue
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3
Take the ramp slight right toward IL 137
5.5 mi · 7 min
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4
Turn right onto Buckley Road
1.5 mi · 2 min · Buckley Road
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5
Turn left onto North Skokie Highway
5.6 mi · 7 min · North Skokie Highway
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6
Continue on Skokie Valley Road
3.4 mi · 4 min · Skokie Valley Road
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7
Continue on Skokie Highway
3.8 mi · 4 min · Skokie Highway
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8
Continue on Edens Expressway
13.7 mi · 17 min · Edens Expressway
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9
Continue on Kennedy Expressway
8.1 mi · 12 min · Kennedy Expressway
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10
Continue on Dan Ryan Expressway
1.5 km · 1 min · Dan Ryan Expressway
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11
Take the exit slight right toward 18th Street
1398 ft · 34 sec
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12
Turn slight left onto South Union Avenue
963 ft · 30 sec · South Union Avenue
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13
Turn right onto South Canalport Avenue
154 m · 13 sec · South Canalport Avenue
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14
Turn left onto South Halsted Street
737 ft · 19 sec · South Halsted Street
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15
Turn right onto West Cermak Road
976 ft · 25 sec · West Cermak Road
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16
Turn left
46 m · 11 sec
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17
Turn right
794 ft · 58 sec
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18
Arrive at your destination
0 m · 1 sec
Car Route Details
A richer read on the saved driving route between Winthrop Harbor 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.
Edens Expressway
Continue on Edens Expressway
13.7 mi · 00h 17m
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 Winthrop Harbor and Slight Chance Snow Showers then Mostly Sunny near Chicago.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Winthrop Harbor to Chicago?
The road trip is about 59.5 miles (95.7 km) and usually takes 01h 12m 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?
Highland Park is a useful midpoint, sitting about 25.3 miles from Winthrop Harbor and 34.2 miles from Chicago.
How much longer is the road route than the straight-line distance?
The direct path is about 44.4 miles (71.4 km), while the road route adds roughly 15.1 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 CDT. If you want a more comfortable same-day return, try to leave by 4:06 PM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $7.92 one way or $15.84 round trip. Estimated CO2 is about 18.7 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny around Winthrop Harbor and Slight Chance Snow Showers then Mostly Sunny near Chicago.
Stop Ideas Near Highland Park
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 Highland Park.
Glenview station
Chicago Union Station
La Grange Road
Summit
Flight Path Map
This map shows the direct air route between Winthrop Harbor and Chicago. Straight-line distance: 44.35 mi (71.38 km).
#1 Winthrop Harbor
Village in Illinois, United States
| Population | 6,568 |
| Coordinates | 42.4789100, -87.8236800 |
| Altitude | 194 |
| 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: 96 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 01h 58m |
| 40 mph (64.37 km/h) | 01h 29m |
| 50 mph (80.47 km/h) | 01h 11m |
| 60 mph (96.56 km/h) | 00h 59m |
| 70 mph (112.65 km/h) | 00h 50m |
| 80 mph (129 km/h) | 00h 44m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $7.92 | $15.84 |
| Mid-grade | $4.25 | $8.93 | $17.86 |
| Premium | $4.65 | $9.77 | $19.55 |
| Diesel | $5.30 | $11.14 | $22.28 |
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 · Apr 19, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.