Origin
Highland, IL
Late night in Highland on Wednesday
Local time
5:03 AM
CDT
Current temp
77°F
Unavailable
Live forecast
Trip from Highland, IL to Chicago, IL
Data updated 1 hour ago
Drive Time
5h 10m
Distance
277.7 mi
447 km
Drive Score
8/10
Great drive
Same Day?
Yes, doable
Fuel Cost
$43
one way
EV Charging
Loading...
station data
Best Time to Leave
4 AM
4h 57m
★
6 AM
5h 11m
8 AM
5h 38m
10 AM
5h 20m
12 PM
5h 18m
3 PM
5h 22m
5 PM
5h 37m
8 PM
5h 3m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Highland, IL
Eclipse Chasers
Chicago, IL
Otoniel Alvarado
Trip Overview
Driving from Highland to Chicago spans 277.7 miles across the Illinois landscape. You can expect a travel time of approximately 5 hours and 10 minutes, making this a manageable day trip that does not require an overnight stay. Your journey will take you from the southern part of the state toward the urban hub of the Midwest, primarily utilizing a mix of Poplar Street, Highway 40, and I-70 East. Budgeting around $41 for fuel is a safe estimate for your vehicle's needs on this trek. Whether you are traveling for business or a change of scenery, the route is straightforward enough to complete in a single stretch with one planned stop.
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
138.9 miles from Highland, IL
A natural place for your longest stop of the day , about 2h 33m into the drive .
Loading map...
Drive Character
This trip is defined as a turn-heavy local drive rather than a monotonous interstate sprint. Because the highway share is 0%, you should prepare for a more involved experience behind the wheel that requires consistent attention to shifting road conditions. Navigating local routes like Highway 40 and Poplar Street offers a different pace than typical high-speed transit. You will find that the personality of the road remains consistent throughout the 277.7-mile journey, favoring local transit over long-distance highway cruising. Expect a hands-on driving experience that demands focus as you transition through the Illinois countryside.
Most of the miles stay on highways, which makes pacing and fuel planning easier than turn-by-turn city driving.
There are about 18 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 195.2 miles.
How Hard Is This Drive?
This is a straightforward highway drive that stays mostly on I 57 and US 40. You will hit about 11 points where you need to pay attention to lane position or signs. The trickiest moment comes around 0.7 miles in near US Highway 40.
Route Complexity
5/10
Moderate - straightforward overall, but long enough or busy enough to require pacing
This drive requires moderate attention. Across 277.7 miles you will encounter 11 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.
Where does it get tricky?
The main spots that need attention: at 0.7 miles (US Highway 40): Roundabout - know your exit number before entering; at 4.1 miles (US 40): Navigation decision point; at 72 miles (I 57): Highway fork - watch signs carefully. Lane positioning matters here.
Critical Maneuvers
5 of 11 key pointsThese are the spots where you need to pay the most attention. Preview them before you drive.
4
0.7 mi into trip
|
~1m in
|
US Highway 40
Enter roundabout onto US Highway 40
Roundabout - know your exit number before entering
4
4.1 mi into trip
|
~6m in
|
US 40
Take the ramp onto US 40 toward I-70 East: Effingham
Navigation decision point
Toward I-70 East: Effingham
7
72 mi into trip
|
~1h 20m in
|
I 57
Keep slight left at fork onto I 57 toward I 57 North: Chicago
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
Toward I 57 North: Chicago
6
270.5 mi into trip
|
~4h 58m in
|
I 94 / Dan Ryan Expressway (Express)
Keep slight left at fork onto I 94 / Dan Ryan Expressway (Express) toward I 90 Express, I 94 Express: Pershing Road
Highway fork - watch signs carefully. Multiple destination signs - pick the right one
Toward I 90 Express, I 94 Express: Pershing Roa...
8
276.7 mi into trip
|
~5h 7m in
Take the exit toward Canalport Avenue, Cermak Road
Exit ramp - move to the correct lane early. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Exit 53A
Toward Canalport Avenue, Cermak Road
Main Roads
| Road | Distance | Duration |
|---|---|---|
| I 57 | 195.2 mi | 3h 34m |
| US 40 | 67.9 mi | 1h 13m |
| Dan Ryan Expressway (Express) | 6.2 mi | 8m |
| Dan Ryan Expressway | 3.3 mi | 4m |
| US Highway 40 | 3.3 mi | 5m |
| Poplar Street | 0.7 mi | 1m |
| West Cermak Road | 0.2 mi | <1m |
| South Canalport Avenue | 0.2 mi | <1m |
Longest stretch:
I 57
— 195.2 mi, about 3h 34m
Turn-by-Turn Driving Directions
Step-by-step road directions between Highland, IL and Chicago, IL.
1
Start on this road
104 ft
·
2 sec
·
this road
2
Continue
123 ft
·
2 sec
3
Turn straight onto IL 160
0.7 mi
·
1 min
·
Poplar Street
4
Enter roundabout onto US Highway 40
39 ft
·
0 sec
·
US Highway 40
5
Continue on US Highway 40
3.3 mi
·
5 min
·
US Highway 40
6
Take the ramp onto US 40
68 mi
·
1 hr 13 min
·
US 40
Toward I-70 East: Effingham
7
Keep slight left at fork onto I 57
195 mi
·
3 hr 34 min
·
I 57
Toward I 57 North: Chicago
Use the straight / slight right lanes.
8
Continue on I 94
3.3 mi
·
4 min
·
Dan Ryan Expressway
Use the straight / slight right lanes.
9
Keep slight left at fork onto I 94
6.2 mi
·
8 min
·
Dan Ryan Expressway (Express)
Toward I 90 Express, I 94 Express: Pershing Road
10
Take the exit
0.3 mi
·
39 sec
Exit 53A
Toward Canalport Avenue, Cermak Road
Use the straight / slight right lanes.
11
Turn slight left onto South Ruble Street
243 ft
·
6 sec
·
South Ruble Street
12
Turn slight left
75 ft
·
4 sec
13
Turn left onto South Canalport Avenue
0.2 mi
·
26 sec
·
South Canalport Avenue
14
Turn left onto South Halsted Street
0.1 mi
·
18 sec
·
South Halsted Street
15
Turn right onto West Cermak Road
0.2 mi
·
24 sec
·
West Cermak Road
16
Turn left
152 ft
·
11 sec
17
Turn right
0.2 mi
·
58 sec
18
Arrive at destination
Trip Plan
Since this is a 5-hour and 10-minute drive, departing early in the morning helps you avoid potential congestion as you approach your destination. Plan to utilize your one recommended stop mid-way through the trip to stretch your legs and refuel, keeping your $41 fuel budget in mind. Because this route relies on local roads rather than major interstates, keep a close watch on your GPS to navigate the frequent turns accurately. The flexibility of a single-day trip means you have the freedom to adjust your departure time based on traffic reports. Staying alert is key, as the local road profile requires more active steering than a standard highway route.
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 138.9 miles from Highland, IL, or about 2h 33m into the drive.
The longest continuous stretch on this route runs about 195.2 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 80 miles or 1h 29m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 138.9 miles or 2h 33m 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 11m
Traffic, exits, and arrival timing usually matter more near Chicago, IL than in the middle of the route.
Before You Leave
+
Open the route before leaving Highland, 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 Highland, IL
This is one driving day of about 277.7 miles and 5h 10m.
Your first comfortable stop window is around 80 miles from Highland, 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 57 for about 195.2 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 138.9 mi from Highland, IL · 2h 33m into the drive
Mid-route town
Meal stop
139 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 80 miles helps settle the day before fatigue starts building.
Meal break
The midpoint is around 138.9 miles from Highland, 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 195.2 miles.
Arriving in Chicago, IL
The final approach into Chicago, 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 Chicago, 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
$43.42 one way
$86.83 round trip
$3.97/gal
25.4 MPG avg
97 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.36 | $47.67 | $95.34 |
| premium | $4.89 | $53.44 | $106.88 |
| diesel | $5.61 | $61.31 | $122.63 |
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$43
Meals
$25–$50
Total
$68–$93
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 97.2 kg one way. Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $29 in charging · 1 stop · 67% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 83.3 | 1 | $29.16 | $13.33 |
| Efficient EV | 69.4 | 0 | $24.30 | $11.11 |
| EV Truck/SUV | 111.1 | 1 | $38.88 | $17.77 |
Gas CO2
97 kg
EV CO2
32 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
Chicago, IL
Late night in Chicago on Wednesday
Local time
5:03 AM
CDT
Current temp
58°F
Scattered Showers And Thunderstorms
W 10 mph
75% chance
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
19 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 10m 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.
Frequently Asked Questions
The drive from Highland, IL to Chicago, IL covers 277.7 miles and takes about 5h 10m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are I 57, US 40, Dan Ryan Expressway (Express). Most of the drive stays on highways, so watch for ramps and exits.
This is a comfortable same-day trip.
The midpoint is about 138.9 miles from Highland, IL. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $43.42 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.
An early start around 7-8 AM gets you there with plenty of daylight left. A late afternoon start means arriving after dark. Morning is better.
Plan about 1 meaningful break for fuel, food, or rest. Plan on a short reset every 3 to 4 hours to stay fresh behind the wheel.
This drive requires moderate attention. Across 277.7 miles you will encounter 11 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.
The main spots that need attention: at 0.7 miles (US Highway 40): Roundabout - know your exit number before entering; at 4.1 miles (US 40): Navigation decision point; at 72 miles (I 57): Highway fork - watch signs carefully. Lane positioning matters here.
The route from Highland, IL to Chicago, IL does not surface many named destination signs beyond the main corridor.
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