How far is Chicago, IL from Chester, IL?
The driving distance from Chicago, IL to Chester, IL is about 339.4 miles (546.2 km), with a travel time of about 06h 38m by car.
- The straight-line flight distance is about 295.3 miles (475.3 km).
- For a round trip, plan for roughly 13h 16m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 6:00 AM to 7:30 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 06h 38m.
Starting early still helps, but most travelers will want a longer stop or an overnight stay on a route this long.
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.
City in Illinois, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Mostly Sunny
Sunny
Driving Route Map
The map below follows the saved road route between Chicago and Chester.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chicago and Chester.
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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 right to continue on I 55: Saint Louis, Lake Shore Drive
1820 ft · 44 sec
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8
Keep slight right to continue on I 55 South: St Louis
2604 ft · 1 min
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9
Merge slight left onto Stevenson Expressway
5.6 mi · 8 min · Stevenson Expressway
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10
Continue on Adlai E Stevenson Expressway
1739 ft · 27 sec · Adlai E Stevenson Expressway
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11
Continue on Adlai Stevenson Expressway
128.7 mi · 2 hr 26 min · Adlai Stevenson Expressway
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12
Keep slight right to continue on I 55 South: Saint Louis, Springfield
64.8 mi · 1 hr 10 min
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13
Keep slight left to continue on I 55 South: Saint Louis
77.9 mi · 1 hr 24 min
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14
Take the exit slight right toward IL 159 South: Collinsville
1434 ft · 48 sec
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15
Continue on Vandalia Street
3 mi · 5 min · Vandalia Street
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16
Continue on South Morrison Avenue
1.3 mi · 2 min · South Morrison Avenue
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17
Continue on North Illinois Street
9.8 mi · 15 min · North Illinois Street
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18
Enter the roundabout and take exit 2 toward Illinois Street
55 m · 5 sec · South Illinois Street
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19
Exit the rotary onto South Illinois Street
8.3 mi · 13 min · South Illinois Street
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20
Continue on State Route 159
6.1 mi · 9 min · State Route 159
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21
Continue on North Main Street
1163 ft · 20 sec · North Main Street
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22
Continue on N Main St
810 ft · 14 sec · N Main St
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23
Continue on Main Street
8 mi · 12 min · Main Street
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24
Continue straight
23.3 mi · 29 min
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25
Turn right onto State Street
118 m · 7 sec · State Street
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26
Turn right onto East Stacey Street
38 m · 6 sec · East Stacey Street
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27
Arrive at your destination
0 m · 1 sec · East Stacey Street
Car Route Details
A richer read on the saved driving route between Chicago and Chester.
Long-distance drive
This route is long enough that fuel, rest stops, weather, and timing matter more than any single maneuver.
Adlai Stevenson Expressway
Continue on Adlai Stevenson Expressway
129 mi · 02h 26m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
Better with a longer stop
This route is long enough that most travelers will be better off planning an overnight stay or a more deliberate stop window.
Mostly Sunny leaving Chicago and Sunny near Chester.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chicago to Chester?
The road trip is about 339.4 miles (546.2 km) and usually takes 06h 38m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route is long enough that most travelers will be better off planning an overnight stay or a more deliberate stop window.
What is the halfway point on this route?
Lincoln is a useful midpoint, sitting about 169.8 miles from Chicago and 169.6 miles from Chester.
How much longer is the road route than the straight-line distance?
The direct path is about 295.3 miles (475.3 km), while the road route adds roughly 44.1 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 7:30 AM CDT. Starting early still helps, but most travelers will want a longer stop or an overnight stay on a route this long.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $45.18 one way or $90.35 round trip. Estimated CO2 is about 106.5 kg one way.
What should you check before leaving?
Before you leave, expect Mostly Sunny around Chicago and Sunny near Chester.
Stop Ideas Near Lincoln
Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.
Route 66 Original Alignment- Driveable!
City of Lincoln
Transit and Meeting Points
Useful pickup, handoff, or rendezvous points close to Lincoln.
Lincoln
Springfield station
Uptown Station
Peoria, Illinois
Flight Path Map
This map shows the direct air route between Chicago and Chester. Straight-line distance: 295.33 mi (475.28 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 Chester
City in Illinois
| Population | 8,145 |
| Coordinates | 37.9136600, -89.8220500 |
| Altitude | 204 |
| Country | United States |
End: Chester (-89.82205, 37.91366)
Estimated Travel Time
Distance: 546 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 11h 18m |
| 40 mph (64.37 km/h) | 08h 29m |
| 50 mph (80.47 km/h) | 06h 47m |
| 60 mph (96.56 km/h) | 05h 39m |
| 70 mph (112.65 km/h) | 04h 50m |
| 80 mph (129 km/h) | 04h 14m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $45.18 | $90.35 |
| Mid-grade | $4.25 | $50.95 | $101.90 |
| Premium | $4.65 | $55.75 | $111.51 |
| Diesel | $5.30 | $63.54 | $127.08 |
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.