How far is Winchester, IL from Des Plaines, IL?
The driving distance from Winchester, IL to Des Plaines, IL is about 255.3 miles (410.9 km), with a travel time of about 04h 01m by car.
- The straight-line flight distance is about 213.7 miles (343.9 km).
- For a round trip, plan for roughly 08h 03m 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 04h 01m.
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.
Township in McLean County, Illinois
Route Weather Snapshot
Check the forecast at both ends before you head out.
Showers And Thunderstorms
Showers And Thunderstorms Likely
Driving Route Map
The map below follows the saved road route between Winchester and Des Plaines.
Turn-by-Turn Driving Directions
Step-by-step road directions between Winchester and Des Plaines.
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1
Start on East Cherry Street
3273 ft · 1 min · East Cherry Street
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2
Continue on Illinois Route 106
762 ft · 17 sec · Illinois Route 106
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3
Turn right onto Old Route 36
3.5 mi · 5 min · Old Route 36
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4
Turn straight onto Old US Route 36
772 ft · 16 sec · Old US Route 36
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5
Take the ramp right
1980 ft · 49 sec
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6
Merge slight left
59.2 mi · 1 hr 4 min
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7
Continue straight
20.5 mi · 22 min
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8
Keep slight right to continue on I 55 North: Chicago
29.4 mi · 31 min
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9
Keep slight left to continue on I 55 North, I 74 West: Chicago, Peoria
120.8 mi · 2 hr 14 min
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10
Take the exit slight right toward I 294 Tollway North: Wisconsin
1.6 mi · 3 min
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11
Keep slight left to continue on I 294 North: Wisconsin
1694 ft · 41 sec
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12
Merge slight left onto Tri-State Tollway
4.8 mi · 6 min · Tri-State Tollway
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13
Keep slight left to continue on Tri-State Tollway
11.7 mi · 15 min · Tri-State Tollway
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14
Take the exit slight right toward Touhy Avenue
635 ft · 16 sec
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15
Keep slight left to continue on Touhy Avenue
2694 ft · 1 min
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16
Keep slight left to continue on Touhy Avenue West
688 ft · 17 sec
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17
Keep slight right to continue on Touhy Avenue West
1799 ft · 44 sec
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18
Turn straight onto East Touhy Avenue
99 m · 7 sec · East Touhy Avenue
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19
Turn slight right
103 m · 9 sec
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20
Turn right onto South Des Plaines River Road
1.7 mi · 3 min · South Des Plaines River Road
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21
Turn left onto Henry Avenue
557 ft · 24 sec · Henry Avenue
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22
Arrive at your destination
0 m · 1 sec · Henry Avenue
Car Route Details
A richer read on the saved driving route between Winchester and Des Plaines.
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 55 North
Keep slight left to continue on I 55 North, I 74 West: Chicago, Peoria
121 mi · 02h 14m
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.
Showers And Thunderstorms leaving Winchester and Showers And Thunderstorms Likely near Des Plaines.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Winchester to Des Plaines?
The road trip is about 255.3 miles (410.9 km) and usually takes 04h 01m 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?
Towanda is a useful midpoint, sitting about 128 miles from Winchester and 127.3 miles from Des Plaines.
How much longer is the road route than the straight-line distance?
The direct path is about 213.7 miles (343.9 km), while the road route adds roughly 41.6 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 8:56 AM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $33.98 one way or $67.95 round trip. Estimated CO2 is about 80.1 kg one way.
What should you check before leaving?
Before you leave, expect Showers And Thunderstorms around Winchester and Showers And Thunderstorms Likely near Des Plaines.
Stop Ideas Near Towanda
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
City Hall - Town of Normal
City of Bloomington, Illinois
Bloomington Finance Department
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Towanda.
Uptown Station
Pontiac station
Lincoln
Peoria, Illinois
Flight Path Map
This map shows the direct air route between Winchester and Des Plaines. Straight-line distance: 213.68 mi (343.89 km).
#1 Winchester
County seat of Scott County, Illinois, USA
| Population | 1,466 |
| Coordinates | 39.6297700, -90.4562400 |
| Altitude | 165 |
| Country | United States |
#2 Des Plaines
The most populous city in Cook County, Illinois.
| Population | 58,179 |
| Coordinates | 42.0333600, -87.8834000 |
| Altitude | 193 |
| Country | United States |
End: Henry Avenue (-87.883408, 42.033456)
Estimated Travel Time
Distance: 411 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 08h 30m |
| 40 mph (64.37 km/h) | 06h 22m |
| 50 mph (80.47 km/h) | 05h 06m |
| 60 mph (96.56 km/h) | 04h 15m |
| 70 mph (112.65 km/h) | 03h 38m |
| 80 mph (129 km/h) | 03h 11m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $33.98 | $67.95 |
| Mid-grade | $4.25 | $38.32 | $76.64 |
| Premium | $4.65 | $41.93 | $83.87 |
| Diesel | $5.30 | $47.79 | $95.58 |
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 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.