How far is Chicago, IL from Winchester, IL?
The driving distance from Chicago, IL to Winchester, IL is about 251.5 miles (404.7 km), with a travel time of about 04h 45m by car.
- The straight-line flight distance is about 212.4 miles (341.8 km).
- For a round trip, plan for roughly 09h 30m 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 45m.
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.
Partly Cloudy
Driving Route Map
The map below follows the saved road route between Chicago and Winchester.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chicago and Winchester.
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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 right to continue on I 55: Saint Louis, Lake Shore Drive
1820 ft · 44 sec
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8
Keep slight right to continue on I 55 South: St Louis
2604 ft · 1 min
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9
Merge slight left onto Stevenson Expressway
5.6 mi · 8 min · Stevenson Expressway
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10
Continue on Adlai E Stevenson Expressway
1739 ft · 27 sec · Adlai E Stevenson Expressway
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11
Continue on Adlai Stevenson Expressway
128.7 mi · 2 hr 26 min · Adlai Stevenson Expressway
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12
Keep slight right to continue on I 55 South: Saint Louis, Springfield
64.8 mi · 1 hr 10 min
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13
Keep slight right to continue on I 72 West, US 36 West: Jacksonville
45.4 mi · 49 min
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14
Take the exit slight right toward IL 106: Winchester
2127 ft · 52 sec
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15
Turn straight onto Old US Route 36
2178 ft · 42 sec · Old US Route 36
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16
Turn straight onto Old Route 36
3.5 mi · 5 min · Old Route 36
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17
Turn left onto Illinois Route 106
762 ft · 15 sec · Illinois Route 106
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18
Continue on West Cherry Street
3273 ft · 1 min · West Cherry Street
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19
Arrive at your destination
0 m · 1 sec · East Cherry Street
Car Route Details
A richer read on the saved driving route between Chicago and Winchester.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
Adlai Stevenson Expressway
Continue on Adlai Stevenson Expressway
129 mi · 02h 26m
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 Partly Cloudy near Winchester.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chicago to Winchester?
The road trip is about 251.5 miles (404.7 km) and usually takes 04h 45m 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 125.7 miles from Chicago and 125.8 miles from Winchester.
How much longer is the road route than the straight-line distance?
The direct path is about 212.4 miles (341.8 km), while the road route adds roughly 39.1 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 6:00 AM to 8:00 AM CDT. If you want a more comfortable same-day return, try to leave by 7:30 AM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $33.45 one way or $66.90 round trip. Estimated CO2 is about 78.8 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny around Chicago and Partly Cloudy near Winchester.
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 Chicago and Winchester. Straight-line distance: 212.38 mi (341.79 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 Winchester
County seat of Scott County, Illinois, USA
| Population | 1,466 |
| Coordinates | 39.6297700, -90.4562400 |
| Altitude | 165 |
| Country | United States |
End: Winchester (-90.45624, 39.62977)
Estimated Travel Time
Distance: 405 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 08h 22m |
| 40 mph (64.37 km/h) | 06h 17m |
| 50 mph (80.47 km/h) | 05h 01m |
| 60 mph (96.56 km/h) | 04h 11m |
| 70 mph (112.65 km/h) | 03h 35m |
| 80 mph (129 km/h) | 03h 08m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $33.45 | $66.90 |
| Mid-grade | $4.25 | $37.72 | $75.45 |
| Premium | $4.65 | $41.28 | $82.56 |
| Diesel | $5.30 | $47.05 | $94.09 |
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 23, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.