How far is Windsor, IL from Chicago, IL?
The driving distance from Windsor, IL to Chicago, IL is about 196.2 miles (315.7 km), with a travel time of about 03h 14m by car.
- The straight-line flight distance is about 173.7 miles (279.5 km).
- For a round trip, plan for roughly 06h 29m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 8:00 AM CDT.
Reverse, save, or send this route
This drive is better planned with a longer stop or an overnight stay. Copy the route link, send it to another device, or print a clean version before you head out.
This drive is better planned with a longer stop or an overnight stay.
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 03h 14m.
An early departure helps you fit a real stop into the day without turning the return into a late-night drive.
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.
Human settlement in Iroquois County, Illinois, United States of America
Route Weather Snapshot
Check the forecast at both ends before you head out.
Mostly Sunny
Mostly Sunny
Driving Route Map
The map below follows the saved road route between Windsor and Chicago.
Turn-by-Turn Driving Directions
Step-by-step road directions between Windsor and Chicago.
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1
Start on North Maple Street
1414 ft · 1 min · North Maple Street
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2
Turn left onto Kentucky Avenue
1663 ft · 28 sec · Kentucky Avenue
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3
Continue on Route 16
5.2 mi · 8 min · Route 16
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4
Continue on Illinois Route 16
1.3 mi · 2 min · Illinois Route 16
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5
Continue on Marshall Avenue
1.8 mi · 3 min · Marshall Avenue
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6
Continue on Route 16
1.5 mi · 2 min · Route 16
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7
Continue on Marshall Avenue
1.6 mi · 3 min · Marshall Avenue
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8
Turn left onto South 21st Street
1164 ft · 21 sec · South 21st Street
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9
Turn right onto Charleston Avenue
3.2 mi · 6 min · Charleston Avenue
-
10
Turn right onto I-57 North: Champaign
1422 ft · 49 sec
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11
Merge slight left
168.9 mi · 3 hr 6 min
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12
Continue on Dan Ryan Expressway
3.3 mi · 5 min · Dan Ryan Expressway
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13
Keep slight left to continue on Dan Ryan Expressway (Express)
6.2 mi · 9 min · Dan Ryan Expressway (Express)
-
14
Take the exit slight right toward Canalport Avenue, Cermak Road
1620 ft · 40 sec
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15
Turn slight left onto South Ruble Street
74 m · 7 sec · South Ruble Street
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16
Turn slight left
23 m · 5 sec
-
17
Turn left onto South Canalport Avenue
887 ft · 26 sec · South Canalport Avenue
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18
Turn left onto South Halsted Street
737 ft · 19 sec · South Halsted Street
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19
Turn right onto West Cermak Road
976 ft · 25 sec · West Cermak Road
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20
Turn left
46 m · 11 sec
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21
Turn right
794 ft · 58 sec
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22
Arrive at your destination
0 m · 1 sec
Car Route Details
A richer read on the saved driving route between Windsor and Chicago.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
I-57 North
Merge slight left
169 mi · 03h 06m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A longer out-and-back drive
This is still possible in one day, but it becomes a long driving day. Leaving early and planning your stop window matters more here.
Mostly Sunny leaving Windsor and Mostly Sunny near Chicago.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Windsor to Chicago?
The road trip is about 196.2 miles (315.7 km) and usually takes 03h 14m in normal driving conditions.
Is this a same-day trip or an overnight route?
This is still possible in one day, but it becomes a long driving day. Leaving early and planning your stop window matters more here.
What is the halfway point on this route?
Buckley is a useful midpoint, sitting about 97.7 miles from Windsor and 98.5 miles from Chicago.
How much longer is the road route than the straight-line distance?
The direct path is about 173.7 miles (279.5 km), while the road route adds roughly 22.5 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 6:00 AM to 8:00 AM CDT. If you want a more comfortable same-day return, try to leave by 10:30 AM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $26.10 one way or $52.19 round trip. Estimated CO2 is about 61.5 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny around Windsor and Mostly Sunny near Chicago.
Stop Ideas Near Buckley
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 Buckley.
Gilman
Rantoul
Illinois Terminal
Pontiac station
Flight Path Map
This map shows the direct air route between Windsor and Chicago. Straight-line distance: 173.67 mi (279.49 km).
#1 Windsor
Town in Shelby County, Illinois, United States
| Population | 1,128 |
| Coordinates | 39.4408700, -88.5947800 |
| Altitude | 214 |
| 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: 316 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 06h 32m |
| 40 mph (64.37 km/h) | 04h 54m |
| 50 mph (80.47 km/h) | 03h 55m |
| 60 mph (96.56 km/h) | 03h 16m |
| 70 mph (112.65 km/h) | 02h 48m |
| 80 mph (129 km/h) | 02h 26m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $26.10 | $52.19 |
| Mid-grade | $4.25 | $29.43 | $58.86 |
| Premium | $4.65 | $32.21 | $64.41 |
| Diesel | $5.30 | $36.70 | $73.41 |
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 · May 02, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.