Winchester, IL to Waukegan, IL is 283.2 miles and takes about 5h 24m via I 55 and I 72, with a fuel budget near $44 and enough daylight to finish in a day. This trip stays within Illinois, moving from the Midwest region to another part of the Midwest. Expect this drive to be mostly highway, making it a straightforward option for a single-day trip. Given the relatively short duration and highway focus, it’s a practical choice for getting between these two points efficiently.
Trip Pace
Same-day drive is realistic
A same-day return is possible, but it will make for a full day on the road.
Break Rhythm
1 planned break
Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
Midpoint
141.6 miles from Winchester, IL
A natural place for your longest stop of the day
, about 2h 36m into the drive
.
Main Roads
Road
Distance
Duration
I 55
170.7 mi
3h 7m
I 72
59.2 mi
1h 4m
Tri-State Tollway
41.8 mi
50m
Old Route 36
3.5 mi
5m
Belvidere Road
1.9 mi
2m
Belvidere Street
1.6 mi
3m
East Cherry Street
0.6 mi
1m
South Jackson Street
0.5 mi
1m
Longest stretch:
I 55
— 170.7 mi, about 3h 7m
Traffic on I-55
Hour-of-day weekday pattern from 24 FHWA count stations on your route.
Peak
4 PM
~1,689 veh/hr typical
· worst 2,115
Quietest
2 AM
~152 veh/hr
Peak-to-quiet ratio
11.1×
busier at peak than in the quiet hours
12a6anoon6p11p
Averaged across 52 weeks of 2023 FHWA Travel Monitoring Analysis System data. Weekday hours only (Mon–Fri).
Turn-by-Turn Driving Directions
Step-by-step road directions between Winchester, IL and Waukegan, IL.
1
Start on IL 106
0.6 mi·1 min·East Cherry Street
2
Continue on IL 106
0.1 mi·17 sec·Illinois Route 106
3
Turn right onto Old Route 36
3.5 mi·5 min·Old Route 36
4
Turn straight onto Old US Route 36
0.1 mi·16 sec·Old US Route 36
5
Take the ramp
0.4 mi·48 sec
6
Merge onto I 72; US 36
59 mi·1 hr 4 min·I 72; US 36
7
Continue on I 55
20 mi·21 min·I 55
8
Keep slight right at fork onto I 55
29 mi·31 min·I 55
Toward I 55 North: ChicagoUse the straight / slight right lanes.
9
Keep slight left at fork onto I 55
121 mi·2 hr 14 min·I 55
Toward I 55 North, I 74 West: Chicago, PeoriaUse the straight / slight right lanes.
10
Take the exit
1.6 mi·3 min
Exit 277AToward I 294 Tollway North: WisconsinUse the right lane.
11
Keep slight left at fork
0.3 mi·41 sec
Toward I 294 North: Wisconsin
12
Merge onto I 294
4.8 mi·5 min·Tri-State Tollway
Use the straight / slight right lanes.
13
Keep slight left at fork onto I 294
37 mi·45 min·Tri-State Tollway
Use the straight / slight right lanes.
14
Take the exit
0.4 mi·47 sec
Exit 11AToward IL 120 East: Belvidere RoadUse the straight / slight right lanes.
15
Turn straight onto IL 120
1.9 mi·2 min·Belvidere Road
16
Continue on IL 120
1.6 mi·3 min·Belvidere Street
17
Turn left onto Glen Rock Avenue
0.5 mi·1 min·Glen Rock Avenue
Use the left lane.
18
Turn left onto South Jackson Street
0.5 mi·1 min·South Jackson Street
19
Arrive at destination
North Jackson Street
Trip Plan
For this 5-hour drive, leaving in the morning is ideal to maximize daylight and avoid rush hour traffic around the Chicago metropolitan area. Since it’s a one-day trip, you have flexibility in your timing. Plan for one stop, perhaps around the halfway point or where you feel ready to stretch your legs. Keep an eye on your fuel; the longest stretch is over 170 miles, so topping off before that segment on I 55 is a good idea. The estimated fuel cost is around $44.
Morning Departure
An early start around 7-8 AM gets you there with plenty of daylight left.
Evening Departure
A late afternoon start means arriving after dark. Morning is better.
You can normally do this drive in one day.
Plan roughly 1 meaningful break for fuel, food, and rest.
The halfway point lands around 141.6 miles from Winchester, IL, or about 2h 36m into the drive.
The longest continuous stretch on this route runs about 170.7 miles.
This is a comfortable same-day trip.
Departure
Before you leave
Start with fuel, water, and navigation already sorted so the first hour feels easy.
First stop
Around 62 miles or 1h 9m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 141.6 miles or 2h 36m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 4h 17m
Traffic, exits, and arrival timing usually matter more near Waukegan, IL than in the middle of the route.
Before You Leave
+
Open the route before leaving Winchester, IL so your first major turns are already loaded.
+
Leave with enough water and a charging cable within reach, not packed away.
+
Check your fuel range against the first long segment, especially if you are starting outside city service areas.
Day 1
Settle into the route from Winchester, IL
This is one driving day of about 283.2 miles and 5h 24m.
Your first comfortable stop window is around 62 miles from Winchester, IL.
This route can stay practical as a one-day drive if traffic stays reasonable.
Plan about 1 real break rather than only quick fuel stops.
The longest stretch is on I 55 for about 170.7 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 12
5 decision points cluster between mile 84.5 and 278.3 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
7
84.5 mi into trip|~1h 33m in|I 55
Keep slight right at fork onto I 55 toward I 55 North: Chicago
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
Toward I 55 North: Chicago
8
113.8 mi into trip|~2h 5m in|I 55
Keep slight left at fork onto I 55 toward I 55 North, I 74 West: Chicago, Peoria
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Toward I 55 North, I 74 West: Chicago, Peoria
7
234.6 mi into trip|~4h 19m in
Take the exit toward I 294 Tollway North: Wisconsin
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the right lane.
Exit 277A
Toward I 294 Tollway North: Wisconsin
6
241.3 mi into trip|~4h 29m in|I 294 / Tri-State Tollway
Keep slight left at fork onto I 294 / Tri-State Tollway
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
7
278.3 mi into trip|~5h 14m in
Take the exit toward IL 120 East: Belvidere Road
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the straight / slight right lanes.
Exit 11A
Toward IL 120 East: Belvidere Road
Fuel & Cost
Regular Gas
$41.82 one way
$83.64 round trip
$3.75/gal25.4 MPG avg99 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.14
$46.17
$92.34
premium
$4.72
$52.58
$105.16
diesel
$4.80
$53.47
$106.95
Estimated Tolls: $2.51
Tri-state Tollway
(41.8 mi)$2.51
Toll estimates based on average 2024-2025 rates. EZ-Pass/SunPass discounts may lower the actual cost.
Estimated Trip Cost (one way, 1 person)
Fuel
$42
Tolls
$3
Meals
$25–$50
Total
$69–$94
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 99.1 kg one way.
Prices: EIA weekly data, 2026-07-13.
Driving Electric?
About $30 in charging
· 1 stop
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
85
1
$29.74
$13.59
Efficient EV
70.8
0
$24.78
$11.33
EV Truck/SUV
113.3
1
$39.65
$18.12
Gas CO2
99 kg
EV CO2
33 kg (67% less)
Plan for 1 charging stop. A 30-minute DC fast charge mid-route should be enough to complete the trip comfortably.
DC fast charging avg $0.35/kWh. Home charging avg $0.16/kWh. US grid CO2: 0.39 kg/kWh.
Travel Intel
Current conditions at both ends of the drive.
Forecast as of Jul 17, 2026
Origin
Winchester, IL
Late night
in Winchester on Monday
Local time
1:27 AM
CDT
Current temp
90°F
Scattered Showers And Thunderstorms
WSW 8 mph26% chanceLive forecast
Special Weather Statement
Special Weather Statement issued July 17 at 2:27PM CDT by NWS Quad Cities IA IL
Special Weather Statement
Special Weather Statement issued July 17 at 2:25PM CDT by NWS Quad Cities IA IL
Destination
Waukegan, IL
Late night
in Waukegan on Monday
Local time
1:27 AM
CDT
Current temp
89°F
Patchy Smoke
SSW 10 mph44% chanceLive forecast
Special Weather Statement
Special Weather Statement issued July 17 at 2:27PM CDT by NWS Quad Cities IA IL
Special Weather Statement
Special Weather Statement issued July 17 at 2:25PM CDT by NWS Quad Cities IA IL
Seasonal Notes
Summer travel usually means heavier construction, hotter rest stops, and busier weekend traffic around major cities.
Winter travel shortens daylight, so a route that looks manageable on paper can feel much longer after dark.
Holiday weekends tend to make both departure and arrival windows slower than the raw route time suggests.
Time zone
Same local time
Origin and destination are on the same clock, so arrival timing is easier to judge at a glance.
Temperature spread
1 degrees cooler at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
5h 24m on the road
An early start around 7-8 AM gets you there with plenty of daylight left.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
National Parks Near This Route
Worth a detour if your schedule allows.
Springfield 1908 Race Riot National Monument
National Monument
In August 1908, a large White mob attacked the Black community in Springfield, Illinois. Rioters destroyed homes and businesses and lynched two men. The event led to the founding of the National Assoc...
4 mi from route
~10 min detour
Free
near mile 58.6
In a growing Chicago neighborhood, diverse people and stories intertwined. All were seeking opportunity. Some succeeded. Others were limited—by race, gender, or economic status. Their stories came tog...
16 mi from route
~41 min detour
Free
near mile 234.4
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
With 82% of this route on highways, you'll spend most of your time on I 55 and I 72. The longest continuous stretch without a significant change in road type is 170.7 miles on I 55. You'll likely notice a considerable number of exits and merges as you navigate the highway system. The final portion will transition from the main interstates to the Tri-State Tollway before reaching Waukegan.
82% highway — fuel and pacing are the main things to plan.
19 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 170.7 mi on I 55.
How Hard Is This Drive?
8/10
This is a straightforward highway drive that stays mostly on I 55 and I 72. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 84.5 miles in near I 55.
Driving Effort8/10
Demanding - plan breaks and stay ahead of the key maneuvers
Balances navigation complexity with total wheel time.
This is a demanding drive. With 12 significant decision points across 283.2 miles, you will need to stay alert - especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.
Where does it get tricky?
The main spots that need attention: at 84.5 miles (I 55): Highway fork - watch signs carefully. Lane positioning matters here; at 113.8 miles (I 55): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 234.6 miles: Exit ramp - move to the correct lane early. Lane positioning matters here.
Elevation Profile
Mostly flat terrain
852 ft535 ft
Total Climb
554 ft
Total Descent
444 ft
Highest Point
852 ft
~121.4 mi in
Elevation Range
317 ft
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
On the drive from Winchester, IL to Waukegan, IL, road signs begin pointing toward Peoria along the way.
Waukegan is in the Far North Suburbs of the Chicagoland region of Illinois. It sits on Lake Michigan, has a large harbor, and is the county seat of Lake County, Illinois.
Top landmarks
•Waukegan Public Library — library
•Waukegan Building — office building in Waukegan, Illinois, United States
•Hotel Waukegan — historic hotel in Waukegan, Illinois, USA
Doable as a same-day drive at 5h 24m. Total distance: 283.2 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
5h 24m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (82%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 170.7 miles on I 55. The full list of main roads is in the Roads section above.
Expect about $2.51 in tolls one way, starting with Tri-state Tollway. Most Northeast and Midwest toll agencies accept E-ZPass; in the West and Texas, transponders like TxTag or FasTrak apply. If you do not have a transponder, cashless tolling plates will mail a bill to the vehicle's registered address — usually with a surcharge, so a rental-car toll pass is often cheaper than paying by mail.
Yes — we found about 30 rest areas or service plazas within a short detour of the route (from OpenStreetMap). See the Rest Stops tab under Nearby Places for locations and mile markers. Plan to stretch, use the bathroom, and top off fluids every 2–3 hours on longer drives.
It helps. This route has a higher-than-average number of complex decision points, which get harder in the dark. If the last hour of the trip is on surface roads or mountain grades, aim to arrive at Waukegan, IL before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Only with planning. This is a long drive for kids — consider splitting it into two days rather than pushing through. Plan at least 1 meaningful breaks. There are 30 rest areas along the route for bathroom stops.
The main spots that need attention: at 84.5 miles (I 55): Highway fork - watch signs carefully. Lane positioning matters here; at 113.8 miles (I 55): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 234.6 miles: Exit ramp - move to the correct lane early. Lane positioning matters here.
Yes — Springfield 1908 Race Riot National Monument and Pullman National Historical Park. See the National Parks section for detour distances and tips on detours.
Not recommended in a single day. At 5.4 hours each way, a round trip means 10.8 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Waukegan, IL before the return drive.
