How far is Chicago, IL from Crestwood, IL?
The driving distance from Chicago, IL to Crestwood, IL is about 329.3 miles (530 km), with a travel time of about 06h 11m by car.
- The straight-line flight distance is about 301.2 miles (484.8 km).
- For a round trip, plan for roughly 12h 22m 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 11m.
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.
Township in Douglas County, Illinois
Route Weather Snapshot
Check the forecast at both ends before you head out.
Slight Chance Snow Showers then Mostly Sunny
Sunny
Driving Route Map
The map below follows the saved road route between Chicago and Crestwood.
Turn-by-Turn Driving Directions
Step-by-step road directions between Chicago and Crestwood.
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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 left to continue on I 57 South: Memphis
65.7 mi · 1 hr 11 min
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12
Keep slight right to continue on Ken Gray Expressway
46.8 mi · 50 min · Ken Gray Expressway
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13
Take the exit slight right toward IL 148
1415 ft · 50 sec
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14
Turn right
1.1 km · 1 min
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15
Turn left
1753 ft · 31 sec
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16
Turn right onto Lake Egypt Road
1.5 km · 2 min · Lake Egypt Road
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17
Turn right onto Power Plant Road
2.7 mi · 7 min · Power Plant Road
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18
Turn left onto McKinney Chapel Road
2872 ft · 2 min · McKinney Chapel Road
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19
Turn right onto Ridgeway
86 m · 18 sec · Ridgeway
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20
Turn left onto Pinewood Drive
117 m · 17 sec · Pinewood Drive
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21
Arrive at your destination
0 m · 1 sec · Pinewood Drive
Car Route Details
A richer read on the saved driving route between Chicago and Crestwood.
Long-distance drive
This route is long enough that fuel, rest stops, weather, and timing matter more than any single maneuver.
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.
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.
Slight Chance Snow Showers then Mostly Sunny leaving Chicago and Sunny near Crestwood.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Chicago to Crestwood?
The road trip is about 329.3 miles (530 km) and usually takes 06h 11m 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?
Arcola is a useful midpoint, sitting about 164.8 miles from Chicago and 164.5 miles from Crestwood.
How much longer is the road route than the straight-line distance?
The direct path is about 301.2 miles (484.8 km), while the road route adds roughly 28.1 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 $43.82 one way or $87.64 round trip. Estimated CO2 is about 103.3 kg one way.
What should you check before leaving?
Before you leave, expect Slight Chance Snow Showers then Mostly Sunny around Chicago and Sunny near Crestwood.
Stop Ideas Near Arcola
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 Arcola.
Mattoon station
Illinois Terminal
Effingham
Rantoul
Flight Path Map
This map shows the direct air route between Chicago and Crestwood. Straight-line distance: 301.23 mi (484.78 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 Crestwood
Village in United States of America
| Population | 10,604 |
| Coordinates | 37.6045000, -88.9400700 |
| Altitude | 167 |
| Country | United States |
End: Crestwood (-88.94007, 37.6045)
Estimated Travel Time
Distance: 530 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 10h 58m |
| 40 mph (64.37 km/h) | 08h 13m |
| 50 mph (80.47 km/h) | 06h 35m |
| 60 mph (96.56 km/h) | 05h 29m |
| 70 mph (112.65 km/h) | 04h 42m |
| 80 mph (129 km/h) | 04h 06m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.77 | $43.82 | $87.64 |
| Mid-grade | $4.25 | $49.42 | $98.84 |
| Premium | $4.65 | $54.08 | $108.16 |
| Diesel | $5.30 | $61.63 | $123.26 |
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 19, 2026
Distance to Other Cities
Planning a road trip? See the full trip guide on Trip.ovh — stops, fuel costs, weather, and departure timing.