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
.
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: ChicagoUse 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 53AToward Canalport Avenue, Cermak RoadUse 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 61 miles or 1h 8m 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 61 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.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 11
5 decision points cluster between mile 0.7 and 276.7 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
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
Fuel & Cost
Regular Gas
$43.42 one way
$86.83 round trip
$3.97/gal25.4 MPG avg97 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.
Forecast as of Apr 21, 2026
Origin
Highland, IL
Late night
in Highland on Tuesday
Local time
4:18 AM
CDT
Current temp
54°F
Unavailable
Live forecast
Destination
Chicago, IL
Late night
in Chicago on Tuesday
Local time
4:18 AM
CDT
Current temp
46°F
Mostly Cloudy
SSE 10 to 15 mph0% chanceLive 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
8 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.
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...
3 mi from route
~7 min detour
Free
near mile 268.2
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
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.
99% 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: 195.2 mi on I 57.
How Hard Is This Drive?
5/10
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.
Driving Effort5/10
Moderate - straightforward overall, but long enough or busy enough to require pacing
Balances navigation complexity with total wheel time.
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.
Chicago is the home of the blues and the truth of jazz, the heart of comedy and the idea of the skyscraper. Here, the age of railroads found its center, and airplanes followed suit. "Stormy, Husky, Brawling / City of Big Shoulders," Chicago is a Heartland boomtown, its ethos defined by urban planner Daniel Burnham's immortal vision: "Make no little plans; they have no magic to stir men's blood." It is one of the world's great cities and the third largest city in the United States, behind only New York City and Los Angeles.
As the hub of the Midwest, Chicago is easy to find — its picturesque skyline calls across the waters of Lake Michigan, a first impression that soon reveals world-class museums of art and science, miles of sandy beaches, huge parks and public art, and perhaps the finest downtown collection of modern architecture in the world.
Top landmarks
•Willis Tower — skyscraper in Chicago, Illinois
•Art Institute of Chicago — art museum and school in Chicago, United States
•Wrigley Field — baseball stadium in Chicago, Illinois, USA; home venue of the Chicago Cubs
Doable as a same-day drive at 5h 10m. Total distance: 277.7 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
5h 10m drive, comfortable solo distance.
First-Time Driver
Mostly highway driving (99%). Some complex stretches to watch for.
Frequently Asked Questions
The longest stretch is about 195.2 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.
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. Dedicated rest areas are limited, so plan gas or food stops as your bathroom breaks.
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.
Yes — Pullman National Historical Park. See the National Parks section for detour distances and tips on detours.
Not recommended in a single day. At 5.2 hours each way, a round trip means 10.4 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Chicago, IL before the return drive.
