Chicago, IL to Pleasant Grove, IL is 341.6 miles and takes about 6h 23m via I 57 and IL 37, with a fuel budget near $54 and enough daylight to finish in a day. This trip stays within the Midwest region, entirely within Illinois, making it a straightforward drive. With 99% highway travel, expect a mostly efficient transit. It's a good option if you need to cover ground quickly without leaving the state. This route is recommended for a single day of travel.
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
170.8 miles from Chicago, IL
A natural place for your longest stop of the day
, about 3h 11m into the drive
.
Main Roads
Road
Distance
Duration
I 57
266.5 mi
4h 51m
Ken Gray Expressway
46.8 mi
50m
IL 37
13.5 mi
19m
Dan Ryan Expressway (Express)
8.8 mi
11m
West Vine Street
3.3 mi
4m
Dan Ryan Expressway
0.7 mi
<1m
IL 148
0.7 mi
<1m
West Cermak Road
0.2 mi
<1m
Longest stretch:
I 57
— 266.5 mi, about 4h 51m
Traffic on I-57
Hour-of-day weekday pattern from 32 FHWA count stations on your route.
Peak
3 PM
~1,073 veh/hr typical
· worst 1,461
Quietest
2 AM
~180 veh/hr
Peak-to-quiet ratio
6×
busier at peak than in the quiet hours
12a6anoon6p11p
Averaged across 99 weeks of 2023 FHWA Travel Monitoring Analysis System data. Weekday hours only (Mon–Fri).
Turn-by-Turn Driving Directions
Step-by-step road directions between Chicago, IL and Pleasant Grove, IL.
1
Start on this road
0.2 mi·1 min·this road
2
At end of road, turn right onto West Cermak Road
0.2 mi·26 sec·West Cermak Road
3
Turn left onto South Halsted Street
0.1 mi·17 sec·South Halsted Street
Use the left lane.
4
Turn right onto South Canalport Avenue
285 ft·5 sec·South Canalport Avenue
5
Turn slight right
110 ft·4 sec
6
Take the ramp
455 ft·11 sec
Toward I 90 East, I 94 East
7
Keep slight left at fork
0.2 mi·22 sec
Toward I 90, I 94 East: IndianaUse the slight left / slight right lanes.
8
Merge onto I 90; I 94
0.7 mi·47 sec·Dan Ryan Expressway
Use the straight / slight right lanes.
9
Keep slight left at fork onto I 90; I 94
8.8 mi·11 min·Dan Ryan Expressway (Express)
Toward I 90 Express, I 94 ExpressUse the straight / slight right lanes.
10
Keep slight right at fork onto I 57
201 mi·3 hr 40 min·I 57
Exit 63Toward I 57 South: MemphisUse the slight right lane.
11
Keep slight left at fork onto I 57
66 mi·1 hr 10 min·I 57
Toward I 57 South: Memphis
12
Keep slight right at fork onto I 57
47 mi·50 min·Ken Gray Expressway
13
Take the exit
0.3 mi·50 sec
Exit 45Toward IL 148
14
Turn right onto IL 148
0.7 mi·59 sec·IL 148
15
Continue on IL 37
14 mi·19 min·IL 37
16
Turn slight right
117 ft·4 sec
17
Turn straight onto IL 146
3.3 mi·4 min·West Vine Street
18
Turn right onto Pleasant Grove Road
383 ft·16 sec·Pleasant Grove Road
19
Arrive at destination
Pleasant Grove Road
Trip Plan
Since this is a single-day trip of about 6 hours and 23 minutes, leaving Chicago in the morning should get you to Pleasant Grove with plenty of daylight to spare. You'll want to plan for at least one stop to break up the drive, especially since the longest continuous stretch on I 57 is 266.5 miles. Keep an eye on your fuel gauge, as the estimated cost is $54, and it's always wise to refuel before hitting very long stretches of highway. Pay attention to the transition off I 57 onto IL 37, as this may signal a change in road conditions and speed limits.
Morning Departure
Start early — leave by 6-7 AM to arrive at a reasonable hour.
Evening Departure
This is a long drive — plan for a morning departure or consider splitting it into two days.
You can normally do this drive in one day.
Plan roughly 1 meaningful break for fuel, food, and rest.
The halfway point lands around 170.8 miles from Chicago, IL, or about 3h 11m into the drive.
The longest continuous stretch on this route runs about 266.5 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 75 miles or 1h 26m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 170.8 miles or 3h 11m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 5h 12m
Traffic, exits, and arrival timing usually matter more near Pleasant Grove, IL than in the middle of the route.
Before You Leave
+
Open the route before leaving Chicago, 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 Chicago, IL
This is one driving day of about 341.6 miles and 6h 23m.
Your first comfortable stop window is around 75 miles from Chicago, 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 266.5 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
The midpoint is around 170.8 miles from Chicago, IL, which is a good place for a longer meal and fuel stop.
Before the longest stretch
Fuel check
Top up before I 57 if your tank is already low. That segment runs about 266.5 miles.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
Heads-up: tricky spots
5 of 13
5 decision points cluster between mile 0.2 and 10.4 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
5
0.2 mi into trip|~1m in|West Cermak Road
At end of road, turn right onto West Cermak Road
Navigation decision point
6
0.4 mi into trip|~1m in|South Halsted Street
Turn left onto South Halsted Street
Lane positioning matters here
Use the left lane.
9
0.7 mi into trip|~2m in
Keep slight left at fork toward I 90, I 94 East: Indiana
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight left / slight right lanes.
Toward I 90, I 94 East: Indiana
8
1.6 mi into trip|~3m in|I 90; I 94 / Dan Ryan Expressway (Express)
Keep slight left at fork onto I 90; I 94 / Dan Ryan Expressway (Express) toward I 90 Express, I 94 Express
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Toward I 90 Express, I 94 Express
8
10.4 mi into trip|~15m in|I 57
Keep slight right at fork onto I 57 toward I 57 South: Memphis
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight right lane.
Exit 63
Toward I 57 South: Memphis
Fuel & Cost
Regular Gas
$52.96 one way
$105.92 round trip
$3.94/gal25.4 MPG avg120 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.32
$58.07
$116.14
premium
$4.93
$66.28
$132.55
diesel
$5.60
$75.30
$150.60
No toll roads detected on this route.
Estimated Trip Cost (one way, 1 person)
Fuel
$53
Meals
$25–$50
Total
$78–$103
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 119.5 kg one way.
Prices: EIA weekly data, 2026-08-31.
Driving Electric?
About $36 in charging
· 1 stop
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
102.5
1
$35.87
$16.40
Efficient EV
85.4
0
$29.89
$13.66
EV Truck/SUV
136.6
1
$47.82
$21.86
Gas CO2
120 kg
EV CO2
40 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 Aug 24, 2026
Origin
Chicago, IL
Morning
in Chicago on Friday
Local time
6:20 AM
CDT
Current temp
59°F
Mostly Clear
NW 0 to 5 mph0% chanceLive forecast
Flood Warning
Flood Warning issued August 23 at 9:48PM EDT until August 26 at 8:00PM EDT by NWS Indianapolis IN
Flood Warning
Flood Warning issued August 23 at 9:48PM EDT until August 28 at 8:27PM EDT by NWS Indianapolis IN
Destination
Pleasant Grove, IL
Morning
in Pleasant Grove on Friday
Local time
6:20 AM
CDT
Current temp
59°F
Partly Cloudy then Patchy Fog
N 1 mph0% chanceLive forecast
Flood Warning
Flood Warning issued August 23 at 9:48PM EDT until August 26 at 8:00PM EDT by NWS Indianapolis IN
Flood Warning
Flood Warning issued August 23 at 9:48PM EDT until August 28 at 8:27PM EDT by NWS Indianapolis IN
71°F
Shelbyville, IL
171 mi in
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
Very similar conditions
Both ends of the route are sitting at about the same temperature right now.
Road read
6h 23m on the road
Start early — leave by 6-7 AM to arrive at a reasonable hour.
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...
Park data from the National Park Service API. Alerts update every 2 hours.
More Details
What kind of drive is this?
This drive is almost entirely on highways, with 99% of the 341.6 miles on expressways. You'll spend most of your time on I 57, including a long stretch of 266.5 miles. The Ken Gray Expressway and IL 37 make up the remaining portion, likely transitioning you to surface roads as you approach your destination. Expect a consistent cruising experience with frequent exits on the main highway.
99% highway — fuel and pacing are the main things to plan.
19 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 266.5 mi on I 57.
How Hard Is This Drive?
6/10
This is a straightforward highway drive that stays mostly on I 57 and Ken Gray Expressway. You will hit about 13 points where you need to pay attention to lane position or signs. The trickiest moment comes around 0.2 miles in near West Cermak Road.
Driving Effort6/10
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 341.6 miles you will encounter 13 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 0.2 miles (West Cermak Road): Navigation decision point; at 0.4 miles (South Halsted Street): Lane positioning matters here; at 0.7 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
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 6h 23m. Total distance: 341.6 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
6h 23m drive, plan rest stops for pacing.
Frequently Asked Questions
The longest stretch is about 266.5 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.
It helps. This route has a higher-than-average number of complex decision points, which get harder in the dark. If the last hour of the trip is on surface roads or mountain grades, aim to arrive at Pleasant Grove, IL before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
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 0.2 miles (West Cermak Road): Navigation decision point; at 0.4 miles (South Halsted Street): Lane positioning matters here; at 0.7 miles: Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one.
Yes — Pullman National Historical Park. See the National Parks section for detour distances and tips on detours.
Not recommended in a single day. At 6.4 hours each way, a round trip means 12.8 hours of driving — that is an unsafe level of fatigue for most drivers. Plan at least one night at Pleasant Grove, IL before the return drive.
