How far is Niles, IL from Winchester, IL?
The driving distance from Niles, IL to Winchester, IL is about 257.8 miles (414.9 km), with a travel time of about 04h 53m by car.
- The straight-line flight distance is about 215.6 miles (347 km).
- For a round trip, plan for roughly 09h 47m 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 53m.
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.
Rain Showers
Showers And Thunderstorms
Driving Route Map
The map below follows the saved road route between Niles and Winchester.
Turn-by-Turn Driving Directions
Step-by-step road directions between Niles and Winchester.
-
1
Start on North Waukegan Road
2122 ft · 44 sec · North Waukegan Road
-
2
Continue on North Milwaukee Avenue
155 m · 17 sec · North Milwaukee Avenue
-
3
Turn right onto West Touhy Avenue
3.5 mi · 7 min · West Touhy Avenue
-
4
Turn left onto South Des Plaines River Road
56 m · 4 sec · South Des Plaines River Road
-
5
Take the ramp slight right toward I 294 South: Indiana
2265 ft · 55 sec
-
6
Merge slight left onto Tri-State Tollway
11.5 mi · 15 min · Tri-State Tollway
-
7
Keep slight left to continue on Tri-State Tollway
4.8 mi · 6 min · Tri-State Tollway
-
8
Keep slight right to continue on Tri-State Tollway
1.2 mi · 1 min · Tri-State Tollway
-
9
Take the exit slight right toward I 55: Chicago, St. Louis
1 km · 1 min
-
10
Keep slight right to continue on I 55 South: Saint Louis
2295 ft · 56 sec
-
11
Merge slight left onto Adlai Stevenson Expressway
119.4 mi · 2 hr 13 min · Adlai Stevenson Expressway
-
12
Keep slight right to continue on I 55 South: Saint Louis, Springfield
64.8 mi · 1 hr 10 min
-
13
Keep slight right to continue on I 72 West, US 36 West: Jacksonville
45.4 mi · 49 min
-
14
Take the exit slight right toward IL 106: Winchester
2127 ft · 52 sec
-
15
Turn straight onto Old US Route 36
2178 ft · 42 sec · Old US Route 36
-
16
Turn straight onto Old Route 36
3.5 mi · 5 min · Old Route 36
-
17
Turn left onto Illinois Route 106
762 ft · 15 sec · Illinois Route 106
-
18
Continue on West Cherry Street
3273 ft · 1 min · West Cherry Street
-
19
Arrive at your destination
0 m · 1 sec · East Cherry Street
Car Route Details
A richer read on the saved driving route between Niles 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
Merge slight left onto Adlai Stevenson Expressway
119 mi · 02h 13m
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.
Rain Showers leaving Niles and Showers And Thunderstorms near Winchester.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Niles to Winchester?
The road trip is about 257.8 miles (414.9 km) and usually takes 04h 53m 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 128.8 miles from Niles and 129 miles from Winchester.
How much longer is the road route than the straight-line distance?
The direct path is about 215.6 miles (347 km), while the road route adds roughly 42.2 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 7:12 AM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $42.45 one way or $84.90 round trip. Estimated CO2 is about 80.9 kg one way.
What should you check before leaving?
Before you leave, expect Rain Showers around Niles and Showers And Thunderstorms 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 Niles and Winchester. Straight-line distance: 215.6 mi (346.98 km).
#1 Niles
City in Trumbull County, Ohio
| Population | 28,615 |
| Coordinates | 42.0189200, -87.8028400 |
| Altitude | 194 |
| 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: 415 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 08h 35m |
| 40 mph (64.37 km/h) | 06h 26m |
| 50 mph (80.47 km/h) | 05h 09m |
| 60 mph (96.56 km/h) | 04h 17m |
| 70 mph (112.65 km/h) | 03h 41m |
| 80 mph (129 km/h) | 03h 12m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $4.67 | $42.45 | $84.90 |
| Mid-grade | $5.29 | $48.16 | $96.31 |
| Premium | $5.84 | $53.12 | $106.23 |
| Diesel | $6.57 | $59.80 | $119.59 |
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 · Oct 15, 2026