Waukegan, IL to Pittsfield, IL is 301 miles and takes about 5h 43m via Adlai Stevenson Expressway and I-55, with a fuel budget near $47 and enough daylight to finish in a day. This all-Illinois route travels southwest through the Midwest, primarily on interstate highways. It's a straightforward trip, well-suited for a single day of driving. You'll find the highway travel makes for efficient progress, so you can get to your destination without too much 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
150.5 miles from Waukegan, IL
A natural place for your longest stop of the day
, about 2h 57m 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 Pittsfield, 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 right at fork onto I 72; US 36
62 mi·1 hr 7 min·I 72; US 36
Toward I 72 West, US 36 West: Jacksonville
15
Take the exit
0.2 mi·24 sec
Exit 35Toward US 54, IL 107: Griggsville, Pittsfield
16
Turn slight left onto US 54
5.2 mi·8 min·US 54
Use the straight lane.
17
Turn right onto East Adams Street
0.1 mi·24 sec·East Adams Street
18
Arrive at destination
East Adams Street
Trip Plan
For this 5h 43m drive, leaving Waukegan in the morning will give you ample daylight to reach Pittsfield. With only one recommended stop and a fuel cost estimate of $47, you can easily complete this trip in a single day. The longest stretch without a major change in road type is over 100 miles, so plan your fuel and rest breaks accordingly. Consider topping off your tank before leaving the Waukegan area to ensure you have enough fuel for the initial highway segment.
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 150.5 miles from Waukegan, IL, or about 2h 57m 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 66 miles or 1h 22m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 150.5 miles or 2h 57m 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 41m
Traffic, exits, and arrival timing usually matter more near Pittsfield, 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 301 miles and 5h 43m.
Your first comfortable stop window is around 66 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 15
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
$50.04 one way
$100.09 round trip
$4.22/gal25.4 MPG avg105 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.60
$54.51
$109.02
premium
$5.18
$61.42
$122.84
diesel
$5.35
$63.40
$126.80
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
$50
Tolls
$3
Meals
$25–$50
Total
$78–$103
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 105.3 kg one way.
Prices: EIA weekly data, 2026-06-01.
Driving Electric?
About $32 in charging
· 1 stop
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
90.3
1
$31.61
$14.45
Efficient EV
75.3
0
$26.34
$12.04
EV Truck/SUV
120.4
1
$42.14
$19.26
Gas CO2
105 kg
EV CO2
35 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
2:53 PM
CDT
Current temp
54°F
Chance Rain Showers
N 5 mph49% chanceLive forecast
Special Weather Statement
Special Weather Statement issued June 1 at 5:49AM CDT by NWS Paducah KY
Severe Thunderstorm Watch
Severe Thunderstorm Watch issued June 1 at 5:44AM CDT until June 1 at 9:00AM CDT by NWS St Louis MO
Destination
Pittsfield, IL
Afternoon
in Pittsfield on Wednesday
Local time
2:53 PM
CDT
Current temp
62°F
Chance Showers And Thunderstorms
SE 3 mph38% chanceLive forecast
Special Weather Statement
Special Weather Statement issued June 1 at 5:49AM CDT by NWS Paducah KY
Severe Thunderstorm Watch
Severe Thunderstorm Watch issued June 1 at 5:44AM CDT until June 1 at 9:00AM CDT by NWS St Louis MO
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
8 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 43m 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...
2 mi from route
~6 min detour
Free
near mile 228.3
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...
18 mi from route
~46 min detour
Free
near mile 51.9
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
This trip is mostly highway, with 84% of the 301 miles on interstates like the Adlai Stevenson Expressway and I-55. You'll experience a significant stretch of 119.4 miles on the Adlai Stevenson Expressway before transitioning to other major roads. Expect a high concentration of exits and merges for much of the drive as you navigate between these main arteries.
84% highway — fuel and pacing are the main things to plan.
18 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 15 significant decision points across 301 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
753 ft545 ft
Total Climb
459 ft
Total Descent
378 ft
Highest Point
753 ft
~150.5 mi in
Elevation Range
208 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 Pittsfield, IL, road signs point toward O'hare, St. Louis and Springfield.
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 43m. Total distance: 301 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
5h 43m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (84%). 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 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 Pittsfield, 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 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 5.7 hours each way, a round trip means 11.4 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Pittsfield, IL before the return drive.
