Origin
Chicago, IL
Evening in Chicago on Wednesday
Local time
7:24 PM
CDT
Current temp
51°F
Unavailable
Live forecast
Trip from Chicago, IL to Flagg, IL
Last recalculated Apr 15, 2026
Drive Time
1h 51m
Distance
86.5 mi
139 km
Drive Score
7/10
Good drive
Same Day?
Yes, doable
Fuel Cost
$14
one way
Best Time to Leave
4 AM
1h 43m
★
6 AM
1h 52m
8 AM
2h 8m
10 AM
1h 57m
12 PM
1h 56m
3 PM
1h 58m
5 PM
2h 7m
8 PM
1h 47m
Estimated drive times based on typical traffic patterns. Actual times may vary with weather, construction, and real-time conditions.
Chicago, IL
Otoniel Alvarado
Flagg, IL
Josh Withers
Trip Overview
This 86.5-mile drive from Chicago to Flagg, Illinois, will take you about 1 hour and 51 minutes to complete. Primarily using the Ronald Reagan Memorial Tollway and Eisenhower Expressway, this trip stays within the Midwest region, offering a straightforward journey. With a fuel cost estimated at $14, it’s an economical option for a single-day excursion. Given its relatively short duration and lack of designated stops, this route is perfectly suited for a day trip, allowing for flexibility in your schedule.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Break Rhythm
0 planned breaks
A short stop every 2 to 3 hours is enough for this drive.
Midpoint
43.2 miles from Chicago, IL
A natural place for your longest stop of the day , about 57m into the drive .
Drive Character
Expect a route with a "turn-heavy local drive" profile, despite a significant portion of highway driving. While 16% of the journey is on highways, you'll experience a mix of faster stretches and more intricate local road navigation. The longest uninterrupted segment is 64.3 miles on the Ronald Reagan Memorial Tollway, offering a chance to settle in before transitioning to more varied road conditions. This drive evolves from more direct highway travel to a more engaging local road experience as you approach your destination.
This route has more turning and local-road decision points than a simple highway run.
There are about 17 navigation steps in the underlying route data, so the final approach matters more than the middle miles.
Ronald Reagan Memorial Tollway is the longest continuous segment at about 64.3 miles.
How Hard Is This Drive?
Expect a hands-on drive with frequent turns and local roads rather than long highway stretches. This route has several spots where lane changes, forks, or exits need your full attention. The trickiest moment comes around 2.7 miles in near West Van Buren Street.
Route Complexity
7/10
Demanding - plan breaks and stay ahead of the key maneuvers
This drive requires moderate attention. Across 86.5 miles you will encounter 14 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 2.7 miles (West Van Buren Street): Lane positioning matters here; at 15 miles (I 88; IL 110 / Ronald Reagan Memorial Tollway): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 16.9 miles (I 88; IL 110 / Ronald Reagan Memorial Tollway): Highway fork - watch signs carefully. Lane positioning matters here.
Critical Maneuvers
5 of 14 key pointsThese are the spots where you need to pay the most attention. Preview them before you drive.
6
2.7 mi into trip
|
~6m in
|
West Van Buren Street
Turn left onto West Van Buren Street
Lane positioning matters here
Use the left / straight lanes.
9
15 mi into trip
|
~23m in
|
I 88; IL 110 / Ronald Reagan Memorial Tollway
Keep slight left at fork onto I 88; IL 110 / Ronald Reagan Memorial Tollway toward I 88 West Toll, I 294 South Toll: Aurora, Indiana
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the slight left lane.
Exit 15A
Toward I 88 West Toll, I 294 South Toll: Aurora...
8
16.9 mi into trip
|
~26m in
|
I 88; IL 110 / Ronald Reagan Memorial Tollway
Keep slight right at fork onto I 88; IL 110 / Ronald Reagan Memorial Tollway toward 22nd Street (Cermak Road)
Highway fork - watch signs carefully. Lane positioning matters here
Use the slight right lane.
Exit 138
Toward 22nd Street (Cermak Road)
8
42 mi into trip
|
~56m in
|
I 88; IL 110 / Ronald Reagan Memorial Tollway
Keep slight left at fork onto I 88; IL 110 / Ronald Reagan Memorial Tollway toward I 88 Toll West, IL 47: DeKalb
Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one
Use the straight / slight right lanes.
Toward I 88 Toll West, IL 47: DeKalb
6
79.3 mi into trip
|
~1h 36m in
Take the exit toward IL 251: Rochelle, Mendota
Exit ramp - move to the correct lane early. Multiple destination signs - pick the right one
Exit 76
Toward IL 251: Rochelle, Mendota
Towns Mentioned on Route Signs
Based on OSRM destination-sign hints, not a full list of every settlement the road passes.
Between Chicago, IL and Flagg, IL, road signs point toward Indiana, 22Nd Street (Cermak Road) and Mendota.
Indiana
15 mi in
|
~23m
|
via I 88; IL 110
22Nd Street (Cermak Road)
16.9 mi in
|
~26m
|
via I 88; IL 110
Mendota
79.3 mi in
|
~1h 36m
Main Roads
| Road | Distance | Duration |
|---|---|---|
| Ronald Reagan Memorial Tollway | 64.3 mi | 1h 12m |
| Eisenhower Expressway | 12.1 mi | 16m |
| Lincoln Avenue | 4.1 mi | 7m |
| South Ashland Avenue | 1.7 mi | 3m |
| IL 251 | 1.4 mi | 2m |
| South Grange Road | 1.1 mi | 4m |
| West Cermak Road | 0.8 mi | 1m |
| West Van Buren Street | 0.2 mi | <1m |
Longest stretch:
Ronald Reagan Memorial Tollway
— 64.3 mi, about 1h 12m
Turn-by-Turn Driving Directions
Step-by-step road directions between Chicago, IL and Flagg, IL.
1
Start on this road
0.2 mi
·
1 min
·
this road
2
At end of road, turn left onto West Cermak Road
0.8 mi
·
1 min
·
West Cermak Road
3
Turn right onto South Ashland Avenue
1.7 mi
·
3 min
·
South Ashland Avenue
4
Turn left onto West Van Buren Street
0.2 mi
·
28 sec
·
West Van Buren Street
Use the left / straight lanes.
5
Take the ramp
0.1 mi
·
16 sec
Toward I 290 West
6
Merge onto I 290; IL 110
12 mi
·
16 min
·
Eisenhower Expressway
Use the straight / slight right lanes.
7
Keep slight left at fork onto I 88; IL 110
1.9 mi
·
2 min
·
Ronald Reagan Memorial Tollway
Exit 15A
Toward I 88 West Toll, I 294 South Toll: Aurora, Indiana
Use the slight left lane.
8
Keep slight right at fork onto I 88; IL 110
25 mi
·
30 min
·
Ronald Reagan Memorial Tollway
Exit 138
Toward 22nd Street (Cermak Road)
Use the slight right lane.
9
Keep slight left at fork onto I 88; IL 110
37 mi
·
40 min
·
Ronald Reagan Memorial Tollway
Toward I 88 Toll West, IL 47: DeKalb
Use the straight / slight right lanes.
10
Take the exit
0.4 mi
·
48 sec
Exit 76
Toward IL 251: Rochelle, Mendota
11
Turn right onto IL 251
1.4 mi
·
2 min
·
IL 251
12
Turn right onto IL 38
338 ft
·
9 sec
·
4th Avenue
13
Turn right onto IL 38
394 ft
·
8 sec
·
North 6th Street
14
Turn right onto IL 38
4.1 mi
·
7 min
·
Lincoln Avenue
15
Turn left onto South Grange Road
1.1 mi
·
4 min
·
South Grange Road
16
Turn left onto East Titus Road
62 ft
·
2 sec
·
East Titus Road
17
Arrive at destination
East Titus Road
Trip Plan
For this 1 hour and 51-minute drive, departing Chicago in the morning will help you avoid potential rush hour traffic. Since the route is just 86.5 miles and has no recommended stops, you have the flexibility to depart whenever suits you best. Keep an eye on your fuel levels, as the estimated cost is $14 for the trip. A key tip for this particular drive is to be prepared for the shift from highway speeds to more local road conditions, especially as you get closer to Flagg, IL, as indicated by the "turn-heavy local drive" profile.
Morning Departure
Leave by 9 AM and you'll arrive before lunch.
Evening Departure
Even a 4 PM departure gets you there before dark in summer.
You can normally do this drive in one day.
You may only need one short stretch break if traffic stays light.
The halfway point lands around 43.2 miles from Chicago, IL, or about 57m into the drive.
The longest continuous stretch on this route runs about 64.3 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 19 miles or 28m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 43.2 miles or 57m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 1h 30m
Traffic, exits, and arrival timing usually matter more near Flagg, 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.
Day 1
Settle into the route from Chicago, IL
This is one driving day of about 86.5 miles and 1h 51m.
Your first comfortable stop window is around 19 miles from Chicago, IL.
This route can stay practical as a one-day drive if traffic stays reasonable.
The longest stretch is on Ronald Reagan Memorial Tollway for about 64.3 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Halfway Point
Midpoint
About 43.2 mi from Chicago, IL · 57m into the drive
Mid-route town
Meal stop
43 mi into the route
Best for: Lunch, fuel, and a longer reset
This sits close to the middle of the route, so it works well for the longest stop of the day.
Pacing Suggestions
Fuel and coffee
A short stop after about 19 miles helps settle the day before fatigue starts building.
Meal break
The midpoint is around 43.2 miles from Chicago, IL, which is a good place for a longer meal and fuel stop.
Before the longest stretch
Fuel checkTop up before Ronald Reagan Memorial Tollway if your tank is already low. That segment runs about 64.3 miles.
Arriving in Flagg, IL
The final approach into Flagg, IL usually feels slower than the middle of the drive, so avoid planning your tightest schedule at the very end.
These stop ideas are pacing suggestions — the exact town or exit can change with traffic, hotel plans, and fuel range.
Fuel & Cost
Regular Gas
$13.52 one way
$27.05 round trip
$3.97/gal
25.4 MPG avg
30 kg CO2
| Fuel Type | $/gal | One Way | Round Trip |
|---|---|---|---|
| midgrade | $4.36 | $14.85 | $29.70 |
| premium | $4.89 | $16.65 | $33.29 |
| diesel | $5.61 | $19.10 | $38.20 |
Estimated Tolls: $3.85
Reagan Memorial Tollway
(64.3 mi)
$3.85
Toll estimates based on average 2024-2025 rates. EZ-Pass/SunPass discounts may lower the actual cost.
Estimated Trip Cost (one way, 1 person)
Fuel
$14
Tolls
$4
Meals
$25–$50
Total
$42–$67
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 30.3 kg one way. Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $9 in charging · 0 stops · 67% less CO2
| Vehicle Type | kWh | Stops | DC Fast | Home Charge |
|---|---|---|---|---|
| Average EV | 26 | 0 | $9.08 | $4.15 |
| Efficient EV | 21.6 | 0 | $7.57 | $3.46 |
| EV Truck/SUV | 34.6 | 0 | $12.11 | $5.54 |
Gas CO2
30 kg
EV CO2
10 kg (67% less)
This trip is well within single-charge range for most EVs. No charging stops needed if you start fully charged.
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.
Destination
Flagg, IL
Evening in Flagg on Wednesday
Local time
7:24 PM
CDT
Current temp
40°F
Unavailable
Live 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
11 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
1h 51m on the road
Use the two city cards together: check the sky where you start, then compare it with the local time and temperature at arrival.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
Frequently Asked Questions
The drive from Chicago, IL to Flagg, IL covers 86.5 miles and takes about 1h 51m without stops. Add 15-30 minutes for a fuel or rest stop on longer drives.
The main roads are Ronald Reagan Memorial Tollway, Eisenhower Expressway, Lincoln Avenue. Expect a mix of highway and local road driving.
This is a comfortable same-day trip.
The midpoint is about 43.2 miles from Chicago, IL. Look for rest areas, gas stations, or food options near the halfway mark.
At current regular gas prices, expect to spend about $13.52 one way. This estimate uses 25.4 MPG — your actual cost will vary with your vehicle's fuel efficiency and current gas prices.
Leave by 9 AM and you'll arrive before lunch. Even a 4 PM departure gets you there before dark in summer.
This drive requires moderate attention. Across 86.5 miles you will encounter 14 spots where lane choice or exit timing matters. Not difficult for experienced highway drivers, but worth previewing the tricky sections before you go.
The main spots that need attention: at 2.7 miles (West Van Buren Street): Lane positioning matters here; at 15 miles (I 88; IL 110 / Ronald Reagan Memorial Tollway): Highway fork - watch signs carefully. Lane positioning matters here. Multiple destination signs - pick the right one; at 16.9 miles (I 88; IL 110 / Ronald Reagan Memorial Tollway): Highway fork - watch signs carefully. Lane positioning matters here.
Between Chicago, IL and Flagg, IL, road signs point toward Indiana, 22Nd Street (Cermak Road) and Mendota.
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