Waukegan, IL to Hillsboro, IL is 283.8 miles and takes about 5h 26m via Adlai Stevenson Expressway and I-55, with a fuel budget near $50 and enough daylight to finish in a day. This drive stays within Illinois, moving you from the Midwest's northern edge down into its central plains. Expect a straightforward trip with a significant portion on major interstates, making it a practical choice for a single-day transit. It’s a good option if you need to get from point A to point B efficiently with minimal fuss.
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
141.9 miles from Waukegan, IL
A natural place for your longest stop of the day
, about 2h 47m into the drive
.
Hour-of-day weekday pattern from 12 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 Waukegan, IL and Hillsboro, IL.
1
Start on North Jackson Street
0.5 mi·1 min·North Jackson Street
2
Turn right onto Glen Rock Avenue
0.5 mi·1 min·Glen Rock Avenue
3
Turn right onto Belvidere Street
1.6 mi·3 min·Belvidere Street
4
Continue on IL 120
2.2 mi·3 min·Belvidere Road
Use the straight / right lanes.
5
Take the ramp
0.3 mi·37 sec
Toward I 94 East Toll: Chicago
6
Merge onto I 94
14 mi·15 min·Tri-State Tollway
Use the straight / slight right lanes.
7
Keep slight right at fork onto I 294
23 mi·28 min·Tri-State Tollway
Toward I 294 South Toll: Indiana, O'HareUse the slight right lane.
8
Keep slight left at fork onto I 294
4.8 mi·5 min·Tri-State Tollway
9
Keep slight right at fork onto I 294
1.2 mi·1 min·Tri-State Tollway
Use the straight / slight right lanes.
10
Take the exit
0.6 mi·1 min
Exit 23Toward I 55: Chicago, St. Louis
11
Keep slight right at fork
0.4 mi·56 sec
Toward I 55 South: Saint LouisUse the slight right lane.
12
Merge onto I 55
119 mi·2 hr 13 min·Adlai Stevenson Expressway
Use the straight / slight right lanes.
13
Keep slight right at fork onto I 55
65 mi·1 hr 10 min·I 55
Toward I 55 South: Saint Louis, SpringfieldUse the straight / slight right lanes.
14
Keep slight left at fork onto I 55
40 mi·42 min·I 55
Toward I 55 South: Saint Louis
15
Take the exit
0.5 mi·54 sec
Toward IL 16: Gillespie, Litchfield
16
Turn left
191 ft·5 sec
17
Turn straight onto IL 16
0.8 mi·1 min·County Road 1200 North
18
Continue on IL 16
2.2 mi·3 min·West Union Avenue
19
Continue on IL 16
7.4 mi·11 min·Illinois Route 16
20
Turn right onto West Seward Street
279 ft·12 sec·West Seward Street
21
Arrive at destination
West Seward Street
Trip Plan
Given the 5h 26m estimated drive time, departing Waukegan in the morning will allow you to reach Hillsboro with ample daylight. With only one recommended stop and 82% of the route being highway, you can easily complete this trip in one day. Keep an eye on your fuel gauge, as the estimated cost is $50, and it's always wise to top off before extended highway stretches. Pay attention to the transition from the Tri-State Tollway to I-55, as this is a key point where the road character shifts.
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 141.9 miles from Waukegan, IL, or about 2h 47m into the drive.
The longest continuous stretch on this route runs about 119.4 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 18m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 141.9 miles or 2h 47m 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 26m
Traffic, exits, and arrival timing usually matter more near Hillsboro, IL than in the middle of the route.
Before You Leave
+
Open the route before leaving Waukegan, 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 Waukegan, IL
This is one driving day of about 283.8 miles and 5h 26m.
Your first comfortable stop window is around 62 miles from Waukegan, 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 Adlai Stevenson Expressway for about 119.4 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 14
5 decision points cluster between mile 18.9 and 168.1 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
8
18.9 mi into trip|~25m in|I 294 / Tri-State Tollway
Keep slight right at fork onto I 294 / Tri-State Tollway toward I 294 South Toll: Indiana, O'Hare
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight right lane.
Toward I 294 South Toll: Indiana, O'Hare
6
46.4 mi into trip|~59m in|I 294 / Tri-State Tollway
Keep slight right at fork onto I 294 / Tri-State Tollway
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
6
47.6 mi into trip|~1h 1m in
Take the exit toward I 55: Chicago, St. Louis
Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one
Exit 23
Toward I 55: Chicago, St. Louis
7
48.3 mi into trip|~1h 2m in
Keep slight right at fork toward I 55 South: Saint Louis
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight right lane.
Toward I 55 South: Saint Louis
8
168.1 mi into trip|~3h 16m in|I 55
Keep slight right at fork onto I 55 toward I 55 South: Saint Louis, Springfield
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 South: Saint Louis, Springfield
Fuel & Cost
Regular Gas
$47.18 one way
$94.37 round trip
$4.22/gal25.4 MPG avg99 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.60
$51.40
$102.79
premium
$5.18
$57.91
$115.82
diesel
$5.35
$59.78
$119.55
Estimated Tolls: $2.55
Tri-state Tollway
(42.6 mi)$2.55
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
$47
Tolls
$3
Meals
$25–$50
Total
$75–$100
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 99.3 kg one way.
Prices: EIA weekly data, 2026-06-01.
Driving Electric?
About $30 in charging
· 1 stop
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
85.1
1
$29.80
$13.62
Efficient EV
71
0
$24.83
$11.35
EV Truck/SUV
113.5
1
$39.73
$18.16
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 Jun 1, 2026
Origin
Waukegan, IL
Afternoon
in Waukegan on Wednesday
Local time
2:54 PM
CDT
Current temp
52°F
Partly Cloudy
NE 10 mph0% chanceLive forecast
Flood Warning
Flood Warning issued June 1 at 12:00PM CDT until June 2 at 1:00PM CDT by NWS Paducah KY
Destination
Hillsboro, IL
Afternoon
in Hillsboro on Wednesday
Local time
2:54 PM
CDT
Current temp
58°F
Showers And Thunderstorms Likely then Mostly Clear
NE 6 mph73% chanceLive forecast
Flood Warning
Flood Warning issued June 1 at 12:00PM CDT until June 2 at 1:00PM CDT by NWS Paducah KY
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
6 degrees warmer at arrival
A meaningful temperature swing is a good cue to rethink layers, water, and how soon you want to arrive.
Road read
5h 26m 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
~9 min detour
Free
near mile 225.1
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 48.9
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
This route is primarily highway, with 82% of the drive on major interstates. You'll experience a longest stretch of 119.4 miles on the Adlai Stevenson Expressway, which means extended periods of consistent cruising. Expect to see a dense network of exits for much of the 5h 26m duration, typical of travel through the Midwest's more populated corridors before transitioning to more open interstate driving.
82% highway — fuel and pacing are the main things to plan.
21 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 119.4 mi on Adlai Stevenson Expressway.
How Hard Is This Drive?
8/10
This is a straightforward highway drive that stays mostly on Adlai Stevenson Expressway and I 55. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 18.9 miles in near I 294 / Tri-State Tollway.
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 14 significant decision points across 283.8 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 18.9 miles (I 294 / Tri-State Tollway): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 46.4 miles (I 294 / Tri-State Tollway): Highway fork - watch signs carefully. Lane positioning matters here; at 47.6 miles: Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one.
Elevation Profile
Mostly flat terrain
835 ft518 ft
Total Climb
496 ft
Total Descent
537 ft
Highest Point
835 ft
~162.2 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.
Between Waukegan, IL and Hillsboro, IL, road signs point toward O'hare, St. Louis and Springfield.
O'hare
18.9 mi in|~25m|via I 294
St. Louis
47.6 mi in|~1h 1m
Springfield
168.1 mi in|~3h 16m|via I 55
Detours Along the Way
Tagged by where each one fits in your drive — first break, midpoint, final stretch.
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 26m. Total distance: 283.8 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
5h 26m 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 119.4 miles on Adlai Stevenson Expressway. The full list of main roads is in the Roads section above.
Expect about $2.55 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 29 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 Hillsboro, 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 29 rest areas along the route for bathroom stops.
The main spots that need attention: at 18.9 miles (I 294 / Tri-State Tollway): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 46.4 miles (I 294 / Tri-State Tollway): Highway fork - watch signs carefully. Lane positioning matters here; at 47.6 miles: Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one.
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 10.9 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Hillsboro, IL before the return drive.
