Origin
Waukegan, IL
Afternoon in Waukegan on Sunday
Local time
2:56 PM
CDT
Current temp
43°F
Unavailable
Live forecast
Trip from Waukegan, IL to Anna, IL
Drive Time
7h 15m
Distance
385.3 mi
620 km
Drive Score
8/10
Great drive
Same Day?
Yes, doable
Fuel Cost
$59
one way
Best Time to Leave
4 AM
7h 5m
★
6 AM
7h 16m
8 AM
7h 37m
10 AM
7h 23m
12 PM
7h 21m
3 PM
7h 24m
5 PM
7h 36m
8 PM
7h 9m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Anna, IL
Stéphane Tendon
Trip Overview
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 .
Drive Character
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.
Most of the miles stay on highways, which makes pacing and fuel planning easier than turn-by-turn city driving.
There are about 20 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
I 57 is the longest continuous segment at about 266.5 miles.
How Hard Is This Drive?
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 1.2 miles in near South Lewis Avenue.
Route Complexity
7/10
Demanding - plan breaks and stay ahead of the key maneuvers
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 1.2 miles (South Lewis Avenue): Lane positioning matters here; 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.
Critical Maneuvers
5 of 12 key pointsThese are the spots where you need to pay the most attention. Preview them before you drive.
5
1.2 mi into trip
|
~3m in
|
South Lewis Avenue
Turn left onto South Lewis Avenue
Lane positioning matters here
Use the none lane.
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 none lane.
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
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
Use the none lane.
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
Use the none lane.
8
Continue on US 41
3.8 mi
·
4 min
·
Skokie Highway
Use the none / straight / slight right lanes.
9
Continue on I 94; US 41
14 mi
·
17 min
·
Edens Expressway
Use the none / straight / slight right lanes.
10
Continue on I 90; I 94
8.1 mi
·
11 min
·
Kennedy Expressway
Use the none lane.
11
Continue on I 90; I 94
2.4 mi
·
2 min
·
Dan Ryan Expressway
Use the none lane.
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 Express
Use the none lane.
13
Keep slight right at fork onto I 57
201 mi
·
3 hr 40 min
·
I 57
Exit 63
Toward I 57 South: Memphis
Use 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.
Halfway Point
Midpoint
About 192.6 mi from Waukegan, IL · 3h 44m into the drive
Mid-route town
Meal stop
193 mi into the route
Best for: Lunch, fuel, and a longer reset
This sits close to the middle of the route, so it works well for the longest stop of the day.
Pacing Suggestions
Fuel and coffee
A short stop after about 85 miles helps settle the day before fatigue starts building.
Meal break
The midpoint is around 192.6 miles from Waukegan, IL, which is a good place for a longer meal and fuel stop.
Before the longest stretch
Fuel checkTop up before I 57 if your tank is already low. That segment runs about 266.5 miles.
Arriving in Anna, IL
The final approach into Anna, IL usually feels slower than the middle of the drive, so avoid planning your tightest schedule at the very end.
Try to arrive with enough fuel left to skip an immediate station stop unless you already know the area around Anna, IL.
After long uninterrupted mileage, take five minutes before the last urban segment to reset and refocus on exits, merges, and city traffic.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
Fuel & Cost
Regular Gas
$58.52 one way
$117.05 round trip
$3.86/gal
25.4 MPG avg
135 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.25 | $64.51 | $129.03 |
| premium | $4.80 | $72.74 | $145.47 |
| diesel | $5.64 | $85.60 | $171.20 |
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$59
Meals
$25–$50
Total
$84–$109
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, 2026-04-06.
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.
Destination
Anna, IL
Afternoon in Anna on Sunday
Local time
2:56 PM
CDT
Current temp
58°F
Unavailable
Live forecast
Along the Route
78°F
Akron, IL
193 mi in
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.
Frequently Asked Questions
The drive from Waukegan, IL to Anna, IL covers 385.3 miles and takes about 7h 15m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are I 57, Ken Gray Expressway, Edens Expressway. Most of the drive stays on highways, so watch for ramps and exits.
This is a comfortable same-day trip.
The midpoint is about 192.6 miles from Waukegan, IL. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $58.52 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.
Start early — leave by 6-7 AM to arrive at a reasonable hour. This is a long drive — plan for a morning departure or consider splitting it into two days.
Plan about 2 meaningful breaks for fuel, food, or rest. Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
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.
The main spots that need attention: at 1.2 miles (South Lewis Avenue): Lane positioning matters here; 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.
The route from Waukegan, IL to Anna, IL does not surface many named destination signs beyond the main corridor.
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