How far is Waukegan, IL from Winchester, IL?
The driving distance from Waukegan, IL to Winchester, IL is about 283.5 miles (456.2 km), with a travel time of about 05h 24m by car.
- The straight-line flight distance is about 232.8 miles (374.7 km).
- For a round trip, plan for roughly 10h 48m 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 05h 24m.
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.
City in Illinois
Route Weather Snapshot
Check the forecast at both ends before you head out.
Mostly Sunny
Partly Cloudy
Driving Route Map
The map below follows the saved road route between Waukegan and Winchester.
Turn-by-Turn Driving Directions
Step-by-step road directions between Waukegan and Winchester.
-
1
Start on North Jackson Street
2647 ft · 1 min · North Jackson Street
-
2
Turn right onto Glen Rock Avenue
2495 ft · 1 min · Glen Rock Avenue
-
3
Turn right onto Belvidere Street
1.6 mi · 3 min · Belvidere Street
-
4
Continue on Belvidere Road
2.2 mi · 3 min · Belvidere Road
-
5
Take the ramp slight right toward I 94 East Toll: Chicago
1511 ft · 37 sec
-
6
Merge slight left onto Tri-State Tollway
13.9 mi · 16 min · Tri-State Tollway
-
7
Keep slight right to continue on Tri-State Tollway
22.7 mi · 29 min · Tri-State Tollway
-
8
Keep slight left to continue on Tri-State Tollway
4.8 mi · 6 min · Tri-State Tollway
-
9
Keep slight right to continue on Tri-State Tollway
1.2 mi · 1 min · Tri-State Tollway
-
10
Take the exit slight right toward I 55: Chicago, St. Louis
1 km · 1 min
-
11
Keep slight right to continue on I 55 South: Saint Louis
2295 ft · 56 sec
-
12
Merge slight left onto Adlai Stevenson Expressway
119.4 mi · 2 hr 13 min · Adlai Stevenson Expressway
-
13
Keep slight right to continue on I 55 South: Saint Louis, Springfield
64.8 mi · 1 hr 10 min
-
14
Keep slight right to continue on I 72 West, US 36 West: Jacksonville
45.4 mi · 49 min
-
15
Take the exit slight right toward IL 106: Winchester
2127 ft · 52 sec
-
16
Turn straight onto Old US Route 36
2178 ft · 42 sec · Old US Route 36
-
17
Turn straight onto Old Route 36
3.5 mi · 5 min · Old Route 36
-
18
Turn left onto Illinois Route 106
762 ft · 15 sec · Illinois Route 106
-
19
Continue on West Cherry Street
3273 ft · 1 min · West Cherry Street
-
20
Arrive at your destination
0 m · 1 sec · East Cherry Street
Car Route Details
A richer read on the saved driving route between Waukegan 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.
Mostly Sunny leaving Waukegan 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 Waukegan to Winchester?
The road trip is about 283.5 miles (456.2 km) and usually takes 05h 24m 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?
Chenoa is a useful midpoint, sitting about 141.7 miles from Waukegan and 141.8 miles from Winchester.
How much longer is the road route than the straight-line distance?
The direct path is about 232.8 miles (374.7 km), while the road route adds roughly 50.7 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 6:12 AM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $37.71 one way or $75.42 round trip. Estimated CO2 is about 88.9 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny around Waukegan and Partly Cloudy near Winchester.
Stop Ideas Near Chenoa
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 Chenoa.
Pontiac station
Uptown Station
Dwight station
Gilman
Flight Path Map
This map shows the direct air route between Waukegan and Winchester. Straight-line distance: 232.83 mi (374.71 km).
#1 Waukegan
The second most populous city in Lake County, Illinois.
| Population | 85,453 |
| Coordinates | 42.3636300, -87.8447900 |
| Altitude | 199 |
| 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: 456 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 09h 26m |
| 40 mph (64.37 km/h) | 07h 05m |
| 50 mph (80.47 km/h) | 05h 40m |
| 60 mph (96.56 km/h) | 04h 43m |
| 70 mph (112.65 km/h) | 04h 02m |
| 80 mph (129 km/h) | 03h 32m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $37.71 | $75.42 |
| Mid-grade | $4.25 | $42.53 | $85.06 |
| Premium | $4.65 | $46.54 | $93.08 |
| Diesel | $5.30 | $53.04 | $106.08 |
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.