How far is Chicago, IL from Highland, IL?
The driving distance from Chicago, IL to Highland, IL is about 277.7 miles (446.9 km), with a travel time of about 05h 10m by car.
- The straight-line flight distance is about 239.8 miles (386 km).
- For a round trip, plan for roughly 10h 20m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 8:00 AM CDT.
Reverse, save, or send this route
This drive is better planned with a longer stop or an overnight stay. Copy the route link, send it to another device, or print a clean version before you head out.
This drive is better planned with a longer stop or an overnight stay.
Flight Distance
Driving Distance
Gas Cost Calculator
Leave and Arrive Planner
Pick a departure time to see your estimated arrival and same-day return window.
Drive time stays fixed at 05h 10m.
An early departure helps you fit a real stop into the day without turning the return into a late-night drive.
You are leaving earlier than the recommended window, which gives you extra margin for breaks and traffic.
Halfway Point
A useful midpoint for breaks, coffee, or meeting in the middle.
Route Weather Snapshot
Check the forecast at both ends before you head out.
Mostly Sunny
Mostly Sunny
Driving Route Map
The map below follows the saved road route between Chicago and Highland.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chicago and Highland.
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1
Start on the route
943 ft · 1 min
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2
At the end of the road, turn right onto West Cermak Road
947 ft · 26 sec · West Cermak Road
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3
Turn left onto South Halsted Street
737 ft · 17 sec · South Halsted Street
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4
Turn right onto South Canalport Avenue
87 m · 6 sec · South Canalport Avenue
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5
Turn slight right
34 m · 5 sec
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6
Take the ramp straight toward I 90 East, I 94 East
139 m · 11 sec
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7
Keep slight left to continue on I 90, I 94 East: Indiana
929 ft · 23 sec
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8
Merge slight left onto Dan Ryan Expressway
1.2 km · 48 sec · Dan Ryan Expressway
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9
Keep slight left to continue on Dan Ryan Expressway (Express)
8.8 mi · 12 min · Dan Ryan Expressway (Express)
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10
Keep slight right to continue on I 57 South: Memphis
200.8 mi · 3 hr 41 min
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11
Keep slight right to continue on I 70 West: Saint Louis
61.7 mi · 1 hr 7 min
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12
Take the exit slight right toward US 40, IL 143: Pierron, Highland
1685 ft · 42 sec
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13
Turn left onto Steiner Road
1396 ft · 24 sec · Steiner Road
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14
Continue on US Highway 40
3.3 mi · 5 min · US Highway 40
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15
Enter the roundabout and take exit 3 toward Poplar Street
75 m · 4 sec · Poplar Street
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16
Exit the roundabout onto Poplar Street
1.1 km · 1 min · Poplar Street
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17
Enter the roundabout toward the route
87 m · 6 sec
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18
Arrive at your destination
0 m · 1 sec
Car Route Details
A richer read on the saved driving route between Chicago and Highland.
Highway-focused drive
Most of the mileage stays on named highways, so the important moments are ramps, exits, merges, and the final local approach.
I 57 South
Keep slight right to continue on I 57 South: Memphis
201 mi · 03h 41m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A longer out-and-back drive
This is still possible in one day, but it becomes a long driving day. Leaving early and planning your stop window matters more here.
Mostly Sunny leaving Chicago and Mostly Sunny near Highland.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chicago to Highland?
The road trip is about 277.7 miles (446.9 km) and usually takes 05h 10m in normal driving conditions.
Is this a same-day trip or an overnight route?
This is still possible in one day, but it becomes a long driving day. Leaving early and planning your stop window matters more here.
What is the halfway point on this route?
Savoy is a useful midpoint, sitting about 138.9 miles from Chicago and 138.8 miles from Highland.
How much longer is the road route than the straight-line distance?
The direct path is about 239.8 miles (386 km), while the road route adds roughly 37.9 extra miles because roads do not follow the straight air line.
When is the best time to leave for this route?
A good departure window is usually 6:00 AM to 8:00 AM CDT. If you want a more comfortable same-day return, try to leave by 6:40 AM CDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $36.96 one way or $73.91 round trip. Estimated CO2 is about 87.1 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny around Chicago and Mostly Sunny near Highland.
Stop Ideas Near Savoy
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Savoy.
Illinois Terminal
Rantoul
Danville, Illinois
Mattoon station
Flight Path Map
This map shows the direct air route between Chicago and Highland. Straight-line distance: 239.84 mi (385.99 km).
#1 Chicago
The third most populous city in the United States and the center of the Chicago metropolitan area.
| Population | 2,677,643 |
| Coordinates | 41.850033, -87.6500523 |
| Altitude | 179 |
| Country | United States |
#2 Highland
City in Madison County, Illinois, United States
| Population | 10,017 |
| Coordinates | 38.7394900, -89.6712000 |
| Altitude | 161 |
| Country | United States |
End: Highland (-89.6712, 38.73949)
Estimated Travel Time
Distance: 447 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 09h 15m |
| 40 mph (64.37 km/h) | 06h 56m |
| 50 mph (80.47 km/h) | 05h 33m |
| 60 mph (96.56 km/h) | 04h 37m |
| 70 mph (112.65 km/h) | 03h 58m |
| 80 mph (129 km/h) | 03h 27m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $36.96 | $73.91 |
| Mid-grade | $4.25 | $41.68 | $83.36 |
| Premium | $4.65 | $45.61 | $91.22 |
| Diesel | $5.30 | $51.98 | $103.96 |
Assumes 8.3 L/100 km (about 28.3 MPG). CO2 is an estimate and varies by vehicle, fuel blend, traffic, and terrain.
Prices in Illinois · Apr 23, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.