How far is Winnetka, IL from Chicago, IL?
The driving distance from Winnetka, IL to Chicago, IL is about 23.2 miles (37.4 km), with a travel time of about 00h 36m by car.
- The straight-line flight distance is about 18.4 miles (29.6 km).
- For a round trip, plan for roughly 01h 12m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 7:00 AM to 7:00 PM CDT.
Reverse, save, or send this route
This is an easy same-day return drive. Copy the route link, send it to another device, or print a clean version before you head out.
This is an easy same-day return drive.
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 00h 36m.
This is a short drive, so your comfort window is wide. Traffic and current weather matter more than the clock.
This departure sits inside the recommended comfort window for the route.
Halfway Point
A useful midpoint for breaks, coffee, or meeting in the middle.
Village in United States of America
Route Weather Snapshot
Check the forecast at both ends before you head out.
Slight Chance Snow Showers then Mostly Sunny
Driving Route Map
The map below follows the saved road route between Winnetka and Chicago.
Turn-by-Turn Driving Directions
Step-by-step road directions between Winnetka and Chicago.
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1
Start on Pine Street
1577 ft · 49 sec · Pine Street
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2
Turn left onto Locust Road
2641 ft · 1 min · Locust Road
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3
At the end of the road, turn right onto Willow Road
1.4 mi · 2 min · Willow Road
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4
Take the ramp slight right toward I 94 East, US 41 South
1035 ft · 25 sec
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5
Merge slight left onto Edens Expressway
10.7 mi · 13 min · Edens Expressway
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6
Continue on Kennedy Expressway
8.1 mi · 12 min · Kennedy Expressway
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7
Continue on Dan Ryan Expressway
1.5 km · 1 min · Dan Ryan Expressway
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8
Take the exit slight right toward 18th Street
1398 ft · 34 sec
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9
Turn slight left onto South Union Avenue
963 ft · 30 sec · South Union Avenue
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10
Turn right onto South Canalport Avenue
154 m · 13 sec · South Canalport Avenue
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11
Turn left onto South Halsted Street
737 ft · 19 sec · South Halsted Street
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12
Turn right onto West Cermak Road
976 ft · 25 sec · West Cermak Road
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13
Turn left
46 m · 11 sec
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14
Turn right
794 ft · 58 sec
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15
Arrive at your destination
0 m · 1 sec
Car Route Details
A richer read on the saved driving route between Winnetka 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
Merge slight left onto Edens Expressway
10.7 mi · 00h 13m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A short regional drive
This route is short enough to handle as a quick errand, commute, or easy same-day return without much planning overhead.
Mostly Sunny leaving Winnetka 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 Winnetka to Chicago?
The road trip is about 23.2 miles (37.4 km) and usually takes 00h 36m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route is short enough to handle as a quick errand, commute, or easy same-day return without much planning overhead.
What is the halfway point on this route?
Lincolnwood is a useful midpoint, sitting about 11.6 miles from Winnetka and 11.6 miles from Chicago.
How much longer is the road route than the straight-line distance?
The direct path is about 18.4 miles (29.6 km), while the road route adds roughly 4.8 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 7:00 AM to 7:00 PM CDT. If you want a more comfortable same-day return, try to leave by 7:18 PM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $3.09 one way or $6.18 round trip. Estimated CO2 is about 7.3 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny around Winnetka and Slight Chance Snow Showers then Mostly Sunny near Chicago.
Stop Ideas Near Lincolnwood
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 Lincolnwood.
Glenview station
Chicago Union Station
La Grange Road
Summit
Flight Path Map
This map shows the direct air route between Winnetka and Chicago. Straight-line distance: 18.37 mi (29.56 km).
#1 Winnetka
Village in Cook County, Illinois, United States
| Population | 12,194 |
| Coordinates | 42.1080800, -87.7359000 |
| Altitude | 199 |
| 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: 37 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 00h 46m |
| 40 mph (64.37 km/h) | 00h 34m |
| 50 mph (80.47 km/h) | 00h 27m |
| 60 mph (96.56 km/h) | 00h 23m |
| 70 mph (112.65 km/h) | 00h 19m |
| 80 mph (129 km/h) | 00h 17m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $3.09 | $6.18 |
| Mid-grade | $4.25 | $3.49 | $6.97 |
| Premium | $4.65 | $3.82 | $7.63 |
| Diesel | $5.30 | $4.35 | $8.70 |
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.