Traveling from Waukegan to Anna covers 385.3 miles across the state of Illinois, typically taking about 7 hours and 15 minutes of drive time. Because this journey is almost entirely highway-focused, you can realistically complete the trip in a single long day if you start early. Budgeting approximately $59 for fuel will get you from the northern reaches of the state down to the southern tip. While it is feasible to power through in one day, splitting the drive can make for a much more relaxed experience. This route provides a direct corridor through the Midwest, moving you from the suburban landscape near Waukegan down into the distinct geography of Southern Illinois.
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
2 planned breaks
Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
Midpoint
192.6 miles from Waukegan, IL
A natural place for your longest stop of the day
, about 3h 44m into the drive
.
Main Roads
Road
Distance
Duration
I 57
266.5 mi
4h 51m
Ken Gray Expressway
61.7 mi
1h 6m
Edens Expressway
13.7 mi
17m
Dan Ryan Expressway (Express)
8.8 mi
11m
Kennedy Expressway
8.1 mi
11m
East Vienna Street
5.8 mi
8m
North Skokie Highway
5.6 mi
6m
Skokie Highway
3.8 mi
4m
Longest stretch:
I 57
— 266.5 mi, about 4h 51m
Turn-by-Turn Driving Directions
Step-by-step road directions between Waukegan, IL and Anna, 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
0.3 mi·33 sec·Belvidere Street
4
Turn left onto South Lewis Avenue
2.9 mi·5 min·South Lewis Avenue
5
Turn right onto IL 137
1.1 mi·1 min·Buckley Road
Use the right lane.
6
Turn left onto US 41
5.6 mi·6 min·North Skokie Highway
Use the left lane.
7
Continue on US 41
3.4 mi·3 min·Skokie Valley Road
8
Continue on US 41
3.8 mi·4 min·Skokie Highway
Use the straight / slight right lanes.
9
Continue on I 94; US 41
14 mi·17 min·Edens Expressway
Use the straight / slight right lanes.
10
Continue on I 90; I 94
8.1 mi·11 min·Kennedy Expressway
Use the straight / slight left lanes.
11
Continue on I 90; I 94
2.4 mi·2 min·Dan Ryan Expressway
Use the straight / slight right lanes.
12
Keep slight left at fork onto I 90; I 94
8.8 mi·11 min·Dan Ryan Expressway (Express)
Toward I 90 Express, I 94 ExpressUse the straight / slight right lanes.
13
Keep slight right at fork onto I 57
201 mi·3 hr 40 min·I 57
Exit 63Toward I 57 South: MemphisUse the slight right lane.
14
Keep slight left at fork onto I 57
66 mi·1 hr 10 min·I 57
Toward I 57 South: Memphis
15
Keep slight right at fork onto I 57
62 mi·1 hr 6 min·Ken Gray Expressway
16
Take the exit
0.2 mi·34 sec
Toward IL 146: Anna, Vienna
17
Turn right onto IL 146
388 ft·6 sec·770N
18
Continue on IL 146
5.8 mi·8 min·East Vienna Street
19
Turn left onto IL 146
34 ft·0 sec·Broad Street
20
Arrive at destination
IL 146
Trip Plan
To keep your 7-hour and 15-minute journey manageable, plan for at least two deliberate stops to stretch your legs and refuel. Since the longest leg of your trip is the 266.5-mile stretch on I-57, try to time your breaks to coincide with the start and end of that corridor to avoid fatigue. Aim to depart early in the morning to avoid potential traffic congestion near the northern end of the route. Keep your $59 fuel budget in mind, and consider filling up before hitting the more rural, southern stretches of the highway where options may be more spread out. Flexibility is key on this highway-focused path, so don't hesitate to pull over if the monotony of the interstate becomes too much.
Morning Departure
Start early — leave by 6-7 AM to arrive at a reasonable hour.
Evening Departure
This is a long drive — plan for a morning departure or consider splitting it into two days.
You can normally do this drive in one day.
Plan roughly 2 meaningful breaks for fuel, food, and rest.
The halfway point lands around 192.6 miles from Waukegan, IL, or about 3h 44m into the drive.
The longest continuous stretch on this route runs about 266.5 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 85 miles or 1h 46m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 192.6 miles or 3h 44m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 6h 8m
Traffic, exits, and arrival timing usually matter more near Anna, 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.
+
Pick one backup stop option before the midpoint in case traffic changes your pacing.
Day 1
Settle into the route from Waukegan, IL
This is one driving day of about 385.3 miles and 7h 15m.
Your first comfortable stop window is around 85 miles from Waukegan, IL.
This route can stay practical as a one-day drive if traffic stays reasonable.
Plan about 2 real breaks rather than only quick fuel stops.
The longest stretch is on I 57 for about 266.5 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 4.1 and 379.2 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
5
4.1 mi into trip|~8m in|IL 137 / Buckley Road
Turn right onto IL 137 / Buckley Road
Lane positioning matters here
Use the right lane.
8
42.2 mi into trip|~56m in|I 90; I 94 / Dan Ryan Expressway (Express)
Keep slight left at fork onto I 90; I 94 / Dan Ryan Expressway (Express) toward I 90 Express, I 94 Express
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Toward I 90 Express, I 94 Express
8
51 mi into trip|~1h 8m in|I 57
Keep slight right at fork onto I 57 toward I 57 South: Memphis
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight right lane.
Exit 63
Toward I 57 South: Memphis
5
251.8 mi into trip|~4h 49m in|I 57
Keep slight left at fork onto I 57 toward I 57 South: Memphis
Highway fork - watch signs carefully
Toward I 57 South: Memphis
5
379.2 mi into trip|~7h 6m in
Take the exit toward IL 146: Anna, Vienna
Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one
Toward IL 146: Anna, Vienna
Fuel & Cost
Regular Gas
$60.24 one way
$120.47 round trip
$3.97/gal25.4 MPG avg135 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.36
$66.14
$132.28
premium
$4.89
$74.15
$148.29
diesel
$5.61
$85.07
$170.14
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$60
Meals
$25–$50
Total
$85–$110
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 134.8 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $40 in charging
· 1 stop
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
115.6
1
$40.46
$18.49
Efficient EV
96.3
1
$33.71
$15.41
EV Truck/SUV
154.1
1
$53.94
$24.66
Gas CO2
135 kg
EV CO2
45 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 Apr 15, 2026
Origin
Waukegan, IL
Evening
in Waukegan on Saturday
Local time
8:29 PM
CDT
Current temp
62°F
Unavailable
Live forecast
Destination
Anna, IL
Evening
in Anna on Saturday
Local time
8:29 PM
CDT
Current temp
77°F
Unavailable
Live forecast
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
15 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
7h 15m on the road
Start early — leave by 6-7 AM to arrive at a reasonable hour.
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.
Pullman National Historical Park
National Historical Park
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...
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
Expect a high-speed, interstate-heavy experience, as 94% of this route consists of highway driving. You will spend the vast majority of your time on I-57, which serves as the backbone of your journey; in fact, you will tackle a single 266.5-mile stretch on this interstate alone. The route also utilizes the Edens Expressway and the Ken Gray Expressway to navigate the transitions between urban and rural segments. It is a straightforward, functional drive designed for efficiency rather than winding backroads. Prepare for a consistent pace behind the wheel as you navigate these major thoroughfares across the state.
94% highway — fuel and pacing are the main things to plan.
20 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 266.5 mi on I 57.
How Hard Is This Drive?
7/10
This is a straightforward highway drive that stays mostly on I 57 and Ken Gray Expressway. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 4.1 miles in near IL 137 / Buckley Road.
Driving Effort7/10
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 385.3 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 4.1 miles (IL 137 / Buckley Road): Lane positioning matters here; at 42.2 miles (I 90; I 94 / Dan Ryan Expressway (Express)): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 51 miles (I 57): Highway fork - watch signs carefully. Lane positioning matters here.
Who Is This Route For?
Weekend Trip
Doable as a same-day drive at 7h 15m. Total distance: 385.3 miles.
Family Friendly
Moderate complexity with 2 natural rest stops along the way.
Solo Traveler
7h 15m drive, plan rest stops for pacing.
Frequently Asked Questions
The longest stretch is about 266.5 miles on I 57. The full list of main roads is in the Roads section above.
We did not find dedicated rest areas on this route. For a drive this long, plan bathroom and stretch breaks around gas stations, fast-food stops, or small-town downtowns — check the Nearby Places section for options.
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 Anna, 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 2 meaningful breaks. Dedicated rest areas are limited, so plan gas or food stops as your bathroom breaks.
The main spots that need attention: at 4.1 miles (IL 137 / Buckley Road): Lane positioning matters here; at 42.2 miles (I 90; I 94 / Dan Ryan Expressway (Express)): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 51 miles (I 57): Highway fork - watch signs carefully. Lane positioning matters here.
Yes — Pullman National Historical Park. See the National Parks section for detour distances and tips on detours.
Not recommended in a single day. At 7.3 hours each way, a round trip means 14.5 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Anna, IL before the return drive.
