How far is Chicago, IL from Windsor, IL?
The driving distance from Chicago, IL to Windsor, IL is about 194.6 miles (313.2 km), with a travel time of about 03h 47m by car.
- The straight-line flight distance is about 173.7 miles (279.5 km).
- For a round trip, plan for roughly 07h 35m 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 47m.
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 Chicago and Windsor.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chicago and Windsor.
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1
Start on the route
943 ft · 1 min
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2
At the end of the road, turn right onto West Cermak Road
947 ft · 26 sec · West Cermak Road
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3
Turn left onto South Halsted Street
737 ft · 17 sec · South Halsted Street
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4
Turn right onto South Canalport Avenue
87 m · 6 sec · South Canalport Avenue
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5
Turn slight right
34 m · 5 sec
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6
Take the ramp straight toward I 90 East, I 94 East
139 m · 11 sec
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7
Keep slight left to continue on I 90, I 94 East: Indiana
929 ft · 23 sec
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8
Merge slight left onto Dan Ryan Expressway
1.2 km · 48 sec · Dan Ryan Expressway
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9
Keep slight left to continue on Dan Ryan Expressway (Express)
8.8 mi · 12 min · Dan Ryan Expressway (Express)
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10
Keep slight right to continue on I 57 South: Memphis
168.6 mi · 3 hr 6 min
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11
Take the exit slight right toward IL 16 West: Mattoon
2489 ft · 1 min
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12
Turn straight onto Charleston Avenue East
2.9 mi · 6 min · Charleston Avenue East
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13
Turn left onto South 21st Street
1164 ft · 24 sec · South 21st Street
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14
Turn right onto Marshall Avenue
1.6 mi · 3 min · Marshall Avenue
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15
Continue on Route 16
1.5 mi · 2 min · Route 16
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16
Continue on Marshall Avenue
1.8 mi · 3 min · Marshall Avenue
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17
Continue on Illinois Route 16
1.3 mi · 2 min · Illinois Route 16
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18
Continue on South 1st Street
5.2 mi · 8 min · South 1st Street
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19
Continue on Kentucky Avenue
1663 ft · 30 sec · Kentucky Avenue
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20
Turn right onto South Maple Street
1414 ft · 1 min · South Maple Street
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21
Arrive at your destination
0 m · 1 sec · North Maple Street
Car Route Details
A richer read on the saved driving route between Chicago and Windsor.
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 South
Keep slight right to continue on I 57 South: Memphis
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 Chicago and Mostly Sunny near Windsor.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chicago to Windsor?
The road trip is about 194.6 miles (313.2 km) and usually takes 03h 47m 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 97.4 miles from Chicago and 97.2 miles from Windsor.
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 20.9 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 9:24 AM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $25.91 one way or $51.81 round trip. Estimated CO2 is about 61.1 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny around Chicago and Mostly Sunny near Windsor.
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 Chicago and Windsor. Straight-line distance: 173.67 mi (279.49 km).
#1 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 |
#2 Windsor
Town in Shelby County, Illinois, United States
| Population | 1,128 |
| Coordinates | 39.4408700, -88.5947800 |
| Altitude | 214 |
| Country | United States |
End: Windsor (-88.59478, 39.44087)
Estimated Travel Time
Distance: 313 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 06h 29m |
| 40 mph (64.37 km/h) | 04h 51m |
| 50 mph (80.47 km/h) | 03h 53m |
| 60 mph (96.56 km/h) | 03h 14m |
| 70 mph (112.65 km/h) | 02h 46m |
| 80 mph (129 km/h) | 02h 25m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $25.91 | $51.81 |
| Mid-grade | $4.25 | $29.22 | $58.44 |
| Premium | $4.65 | $31.97 | $63.95 |
| Diesel | $5.30 | $36.44 | $72.88 |
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.