If you are looking to escape the city for a change of pace, this 161-mile trip from Chicago to Guilford is a manageable day trip. Expect to spend about 3 hours and 37 minutes behind the wheel as you transition from the urban Midwest into the quieter, rural stretches of Illinois. Budget approximately $24 for fuel to cover the journey, which relies on a combination of the Jane Addams Memorial Tollway, the U.S. Grant Memorial Highway, and South Elizabeth Scales Mound Road. Because the total duration is under four hours, you can easily complete this in a single day without needing an overnight stay. While you will only need one primary stop, the route offers enough variety to keep the drive engaging from start to finish.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Break Rhythm
1 planned break
A short stop every 2 to 3 hours is enough for this drive.
Midpoint
80.5 miles from Chicago, IL
A natural place for your longest stop of the day
, about 1h 40m into the drive
.
Main Roads
Road
Distance
Duration
Jane Addams Memorial Tollway
59.4 mi
1h 3m
U.S. Grant Memorial Highway
55.1 mi
1h 9m
South Elizabeth Scales Mound Road
8.1 mi
14m
Kennedy Expressway
7.9 mi
11m
South Galena Avenue
7.3 mi
13m
US 20 Business
3.6 mi
5m
West Higgins Road
3.1 mi
5m
I 39
2.6 mi
2m
Longest stretch:
Jane Addams Memorial Tollway
— 59.4 mi, about 1h 3m
Turn-by-Turn Driving Directions
Step-by-step road directions between Chicago, IL and Guilford, 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
0.2 mi·22 sec·South Canalport Avenue
5
Turn left onto South Ruble Street
0.1 mi·22 sec·South Ruble Street
Use the left lane.
6
Take the ramp
0.3 mi·43 sec
Toward I 90 West, I 94 West
7
Merge onto I 90; I 94
0.9 mi·1 min·Dan Ryan Expressway
Use the straight / slight right lanes.
8
Continue on I 90; I 94
7.9 mi·11 min·Kennedy Expressway
Use the straight / slight right lanes.
9
Take the exit
0.2 mi·28 sec
Exit 43CToward Montrose AvenueUse the slight right lane.
10
Turn left onto West Montrose Avenue
0.7 mi·1 min·West Montrose Avenue
11
Turn right onto North Milwaukee Avenue
1.1 mi·2 min·North Milwaukee Avenue
12
Turn left onto North Northwest Highway
67 ft·1 sec·North Northwest Highway
13
Continue on North Northwest Highway
1.0 mi·1 min·North Northwest Highway
14
Turn slight left onto West Bryn Mawr Avenue
1.8 mi·4 min·West Bryn Mawr Avenue
Use the left lane.
15
Continue on IL 72
3.1 mi·5 min·West Higgins Road
Use the straight / left / right lanes.
16
Take the ramp
0.3 mi·32 sec
Toward I 90 Toll West
17
Merge onto I 90
59 mi·1 hr 3 min·Jane Addams Memorial Tollway
Use the straight / slight right lanes.
18
Take the exit
0.7 mi·1 min
Toward I-39 South, US 51 South: Bloomington
19
Merge onto I 39; US 51
0.5 mi·30 sec·I 39; US 51
20
Continue on I 39; US 20; US 51
2.1 mi·2 min·I 39; US 20; US 51
21
Keep slight left at fork onto US 20
30 mi·34 min·U.S. Grant Memorial Highway
22
Take the exit onto US 20 Business
3.6 mi·5 min·US 20 Business
Toward US 20 BUS: Freeport
23
Turn slight right onto US 20 Business
7.3 mi·13 min·South Galena Avenue
24
Turn left onto US 20
14 mi·19 min·U.S. Grant Memorial Highway
25
Continue on US 20; IL 78
2.1 mi·3 min·East North Avenue
26
Continue on US 20
6.4 mi·8 min·U.S. Grant Memorial Highway
27
Continue on US 20
0.5 mi·1 min·East Woodbine Street
28
Continue on US 20
4.6 mi·6 min·U.S. Grant Memorial Highway
29
Continue on US 20
0.4 mi·1 min·South Main Street
30
Turn straight onto US 20
0.1 mi·20 sec·Diagonal Street
31
Continue on US 20
0.7 mi·1 min·West Madison Street
32
Turn right onto CR 4
8.1 mi·14 min·South Elizabeth Scales Mound Road
33
Turn left onto West Rawlins Road
1.9 mi·4 min·West Rawlins Road
34
Continue on West Guilford Road
0.4 mi·56 sec·West Guilford Road
35
Arrive at destination
West Guilford Road
Trip Plan
To make the most of your day, aim to depart early to avoid lingering city traffic, which will help you reach your destination with plenty of daylight to spare. Since this is a 161-mile trek, plan for at least one dedicated stop to stretch your legs and refuel before hitting the more winding local segments. The flexibility of a shorter drive means you don't have to rush, so take advantage of the ability to pace yourself according to local road conditions. Pay close attention to your navigation when switching from the U.S. Grant Memorial Highway to South Elizabeth Scales Mound Road, as the turn-heavy nature of the final stretch can be easy to miscalculate if you aren't watching your speed. Keeping your fuel costs around $24 ensures you have a straightforward budget for the road ahead.
Morning Departure
An early start around 7-8 AM gets you there with plenty of daylight left.
Evening Departure
A late afternoon start means arriving after dark. Morning is better.
You can normally do this drive in one day.
Plan roughly 1 meaningful break for fuel, food, and rest.
The halfway point lands around 80.5 miles from Chicago, IL, or about 1h 40m into the drive.
The longest continuous stretch on this route runs about 59.4 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 35 miles or 50m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 80.5 miles or 1h 40m in
This is the best place for your longest stop, a real meal, and a full fuel check.
Final approach
Final hour starts around 2h 48m
Traffic, exits, and arrival timing usually matter more near Guilford, 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 161 miles and 3h 37m.
Your first comfortable stop window is around 35 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 Jane Addams Memorial Tollway for about 59.4 miles.
Where to Stop
Rest stops, refuel points, and overnight suggestions along this route.
Place data sourced from public business listings. Hours and availability may vary.
Heads-up: tricky spots
5 of 20
5 decision points cluster between mile 0.2 and 9.9 — 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.
6
0.7 mi into trip|~2m in|South Ruble Street
Turn left onto South Ruble Street
Lane positioning matters here
Use the left lane.
5
1.1 mi into trip|~3m in|I 90; I 94 / Dan Ryan Expressway
Merge onto I 90; I 94 / Dan Ryan Expressway
Merge point - match speed before joining. Lane positioning matters here
Use the straight / slight right lanes.
7
9.9 mi into trip|~16m in
Take the exit toward Montrose Avenue
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the slight right lane.
Exit 43C
Toward Montrose Avenue
Fuel & Cost
Regular Gas
$25.17 one way
$50.34 round trip
$3.97/gal25.4 MPG avg56 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.36
$27.64
$55.27
premium
$4.89
$30.98
$61.97
diesel
$5.61
$35.55
$71.09
Estimated Tolls: $4.16
Jane Addams Memorial Tollway
(59.4 mi)$4.16
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
$25
Tolls
$4
Meals
$25–$50
Total
$54–$79
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 56.3 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $17 in charging
· 0 stops
· 66% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
48.3
0
$16.90
$7.73
Efficient EV
40.3
0
$14.09
$6.44
EV Truck/SUV
64.4
0
$22.54
$10.30
Gas CO2
56 kg
EV CO2
19 kg (66% 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.
Forecast as of Apr 15, 2026
Origin
Chicago, IL
Night
in Chicago on Saturday
Local time
11:36 PM
CDT
Current temp
51°F
Unavailable
Live forecast
Destination
Guilford, IL
Night
in Guilford on Saturday
Local time
11:36 PM
CDT
Current temp
49°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
2 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
3h 37m 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.
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?
Expect a trip that shifts significantly in tone as you leave the metro area. You will start with a 59.4-mile stretch on the Jane Addams Memorial Tollway, which serves as the longest uninterrupted portion of the journey. Once you exit the main highways, which account for only 9% of the total distance, the character of the road changes into a turn-heavy local drive. Navigating the U.S. Grant Memorial Highway and South Elizabeth Scales Mound Road requires more focused attention due to the winding nature of the path. This transition from fast-paced tollways to technical local roads ensures that you stay alert and engaged throughout the latter half of the trip.
Only 9% highway — the rest is turn-by-turn surface driving.
35 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 59.4 mi on Jane Addams Memorial Tollway.
How Hard Is This Drive?
8/10
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 0.2 miles in near West Cermak Road.
Driving Effort8/10
Demanding - plan breaks and stay ahead of the key maneuvers
Balances navigation complexity with total wheel time.
This is a demanding drive. With 20 significant decision points across 161 miles, you will need to stay alert - especially through interchange areas and urban stretches. Consider splitting it into segments if you are not comfortable with fast highway navigation.
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 (South Ruble Street): Lane positioning matters here.
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 3h 37m. Total distance: 161 miles.
Family Friendly
Moderate complexity with 1 natural rest stops along the way.
Solo Traveler
3h 37m drive, comfortable solo distance.
Scenic Drive
Mostly surface roads route profile with national parks nearby.
Frequently Asked Questions
The longest stretch is about 59.4 miles on Jane Addams Memorial Tollway. The full list of main roads is in the Roads section above.
Expect about $4.16 in tolls one way, starting with Jane Addams Memorial Tollway. Most Northeast and Midwest toll agencies accept E-ZPass; in the West and Texas, transponders like TxTag or FasTrak apply. If you do not have a transponder, cashless tolling plates will mail a bill to the vehicle's registered address — usually with a surcharge, so a rental-car toll pass is often cheaper than paying by mail.
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 Guilford, 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 (South Ruble Street): Lane positioning matters here.
Yes — Pullman National Historical Park. See the National Parks section for detour distances and tips on detours.
Possible but tiring. At 3.6 hours each way, an in-and-out day trip would put you behind the wheel for 7.2 hours — manageable with a long break at Guilford, IL, but most travelers stay overnight.
