Traveling the 93.6 miles from Roscoe to Chicago is a straightforward journey that typically takes about 1 hour and 58 minutes. Because this is a relatively short trip, it works perfectly as a single-day excursion without the need for an overnight stay. You can expect to spend roughly $14 on fuel for the trek, making it a budget-friendly option for a day in the city. Since both locations are situated within the Midwest, you will remain in a familiar regional landscape throughout the drive. This route is best suited for travelers who prefer a direct, local approach rather than a long-haul highway expedition. Keeping your schedule flexible allows you to manage the turn-heavy nature of this specific path with ease.
Trip Pace
Same-day drive is realistic
A same-day return is realistic if you keep stops short.
Midpoint
46.8 miles from Roscoe, IL
A natural place for your longest stop of the day
, about 54m into the drive
.
Main Roads
Road
Distance
Duration
Jane Addams Memorial Tollway
69.7 mi
1h 15m
Kennedy Expressway
7.9 mi
11m
Belvidere Road
4.5 mi
7m
West Higgins Avenue
2.7 mi
6m
West Lane Road
1.2 mi
1m
West Higgins Road
1.1 mi
1m
Cumberland flyover
1 mi
1m
Dan Ryan Expressway
0.9 mi
1m
Longest stretch:
Jane Addams Memorial Tollway
— 69.7 mi, about 1h 15m
Turn-by-Turn Driving Directions
Step-by-step road directions between Roscoe, IL and Chicago, IL.
1
Start on Main Street
106 ft·10 sec·Main Street
2
Turn left onto Bridge Street
0.2 mi·22 sec·Bridge Street
3
Continue on Belvidere Road
4.5 mi·7 min·Belvidere Road
4
Turn right
189 ft·6 sec
5
Turn straight onto IL 173
1.2 mi·1 min·West Lane Road
6
Take the ramp
0.5 mi·1 min
7
Merge onto I 39; I 90; US 51
8.3 mi·8 min·Jane Addams Memorial Tollway
8
Keep slight left at fork onto I 90
20 mi·21 min·Jane Addams Memorial Tollway
Use the straight / slight right lanes.
9
Keep slight left at fork onto I 90
41 mi·43 min·Jane Addams Memorial Tollway
Use the straight / slight right lanes.
10
Keep slight right at fork onto I 90
0.3 mi·21 sec·Jane Addams Memorial Tollway
Toward Cumberland AvenueUse the straight / slight right lanes.
11
Keep slight left at fork onto I 90
526 ft·29 sec·Jane Addams Memorial Tollway
12
Merge onto I 90
402 ft·4 sec·Jane Addams Memorial Tollway
13
Take the exit onto Cumberland flyover
1.0 mi·1 min·Cumberland flyover
Exit 79AToward IL 171 South: Cumberland Avenue SouthUse the straight / slight right lanes.
14
Keep slight left at fork
245 ft·8 sec
Toward IL 171 South: Cumberland Avenue
15
Turn right onto IL 171
0.2 mi·28 sec·North Cumberland Avenue
Use the right lane.
16
Continue on IL 171
0.4 mi·1 min·North Cumberland Avenue
Use the left lane.
17
Turn right onto IL 72
1.1 mi·1 min·West Higgins Road
18
Turn right onto IL 72
326 ft·13 sec·North Oriole Avenue
Use the left / right lanes.
19
Turn left onto IL 72
2.7 mi·6 min·West Higgins Avenue
20
Turn right onto North Central Avenue
0.2 mi·25 sec·North Central Avenue
21
Turn left onto West Lawrence Avenue
0.4 mi·42 sec·West Lawrence Avenue
Use the left lane.
22
Turn right onto North Milwaukee Avenue
0.6 mi·1 min·North Milwaukee Avenue
23
Turn left onto West Montrose Avenue
0.5 mi·1 min·West Montrose Avenue
24
Take the ramp
0.3 mi·42 sec
Toward I 90 East, I 94 East
25
Merge onto I 90; I 94
7.9 mi·11 min·Kennedy Expressway
Use the straight / slight left lanes.
26
Continue on I 90; I 94
0.9 mi·1 min·Dan Ryan Expressway
27
Take the exit
0.3 mi·34 sec
Exit 52CToward 18th StreetUse the slight right lane.
28
Turn slight left onto South Union Avenue
0.2 mi·30 sec·South Union Avenue
29
Turn right onto South Canalport Avenue
505 ft·12 sec·South Canalport Avenue
30
Turn left onto South Halsted Street
0.1 mi·18 sec·South Halsted Street
31
Turn right onto West Cermak Road
0.2 mi·24 sec·West Cermak Road
32
Turn left
152 ft·11 sec
33
Turn right
0.2 mi·58 sec
34
Arrive at destination
Trip Plan
Since this drive covers just under 100 miles, you have significant flexibility in your departure time to avoid the worst of local traffic. Given the turn-heavy nature of the roads, checking your GPS for real-time adjustments before you head out is a smart way to ensure a smooth transition into Chicago. Budget your $14 for fuel before leaving Roscoe so you don't have to worry about stops once you get closer to the city. Because there are no designated stops on this route, make sure you are comfortable driving the full duration in one go. A helpful tip for this specific drive is to keep your navigation app active, as the frequent turns can be easy to miss if you are not paying close attention to local signage.
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 46.8 miles from Roscoe, IL, or about 54m into the drive.
The longest continuous stretch on this route runs about 69.7 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 21 miles or 27m in
Use this first pause for coffee, a restroom break, and a quick traffic check ahead.
Halfway reset
Around 46.8 miles or 54m 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 27m
Traffic, exits, and arrival timing usually matter more near Chicago, IL than in the middle of the route.
Before You Leave
+
Open the route before leaving Roscoe, IL so your first major turns are already loaded.
Day 1
Settle into the route from Roscoe, IL
This is one driving day of about 93.6 miles and 1h 58m.
Your first comfortable stop window is around 21 miles from Roscoe, IL.
This route can stay practical as a one-day drive if traffic stays reasonable.
The longest stretch is on Jane Addams Memorial Tollway for about 69.7 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 27
5 decision points cluster between mile 14.9 and 92.6 — GPS handles the exact turns, but know they're coming. Your lane choice matters more than the turn itself.
6
14.9 mi into trip|~20m in|I 90 / Jane Addams Memorial Tollway
Keep slight left at fork onto I 90 / Jane Addams Memorial Tollway
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
6
35.2 mi into trip|~42m in|I 90 / Jane Addams Memorial Tollway
Keep slight left at fork onto I 90 / Jane Addams Memorial Tollway
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
7
75.8 mi into trip|~1h 26m in|I 90 / Jane Addams Memorial Tollway
Keep slight right at fork onto I 90 / Jane Addams Memorial Tollway toward Cumberland Avenue
Highway fork - watch signs carefully. Lane positioning matters here
Use the straight / slight right lanes.
Toward Cumberland Avenue
7
76.3 mi into trip|~1h 27m in|Cumberland flyover
Take the exit onto Cumberland flyover toward IL 171 South: Cumberland Avenue South
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the straight / slight right lanes.
Exit 79A
Toward IL 171 South: Cumberland Avenue South
7
92.6 mi into trip|~1h 55m in
Take the exit toward 18th Street
Exit ramp - move to the correct lane early. Lane positioning matters here
Use the slight right lane.
Exit 52C
Toward 18th Street
Fuel & Cost
Regular Gas
$14.63 one way
$29.27 round trip
$3.97/gal25.4 MPG avg33 kg CO2
Fuel Type
$/gal
One Way
Round Trip
midgrade
$4.36
$16.07
$32.13
premium
$4.89
$18.01
$36.02
diesel
$5.61
$20.67
$41.33
Estimated Tolls: $4.84
Jane Addams Memorial Tollway
(60.9 mi)$4.26
Jane Addams Memorial Tollway
(8.3 mi)$0.58
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
$15
Tolls
$5
Meals
$25–$50
Total
$44–$69
Rough estimate based on US averages. Hotel $80–$140/night, meals $25–$50/day.
Estimated CO2 emission: 32.7 kg one way.
Prices: EIA weekly data, 2026-04-13.
Driving Electric?
About $10 in charging
· 0 stops
· 67% less CO2
Vehicle Type
kWh
Stops
DC Fast
Home Charge
Average EV
28.1
0
$9.83
$4.49
Efficient EV
23.4
0
$8.19
$3.74
EV Truck/SUV
37.4
0
$13.10
$5.99
Gas CO2
33 kg
EV CO2
11 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.
Forecast as of Apr 18, 2026
Origin
Roscoe, IL
Late night
in Roscoe on Sunday
Local time
2:42 AM
CDT
Current temp
48°F
Unavailable
Live forecast
Destination
Chicago, IL
Late night
in Chicago on Sunday
Local time
2:42 AM
CDT
Current temp
46°F
Showers And Thunderstorms
WSW 15 mph98% chanceLive forecast
Flood Warning
Flood Warning issued April 18 at 1:54AM CDT until April 18 at 8:00AM CDT by NWS Chicago IL
Flood Warning
Flood Warning issued April 18 at 1:33AM CDT by NWS Chicago IL
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
1h 58m on the road
The weather snapshot is not static. If you are leaving later, give both cities one more quick forecast check before departure.
Weather data from the National Weather Service. Conditions may change; check closer to your travel date.
More Details
What kind of drive is this?
Expect a turn-heavy local drive rather than a monotonous interstate grind on this 93.6-mile trip. With a 0% highway share, you will be navigating local roads for the duration of the nearly two-hour journey. This configuration means you should stay alert, as the route requires more active steering than a standard freeway cruise. Without long, uninterrupted stretches of highway, the character of the road remains consistent and demands your full attention behind the wheel. Prepare for a hands-on driving experience that prioritizes local navigation over high-speed transit.
Only 9% highway — the rest is turn-by-turn surface driving.
34 navigation steps total — most of the decisions cluster near the start and finish.
Longest single stretch: 69.7 mi on Jane Addams Memorial Tollway.
How Hard Is This Drive?
10/10
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 14.9 miles in near I 90 / Jane Addams Memorial Tollway.
Driving Effort10/10
Demanding - stay alert through the decision-heavy sections
Balances navigation complexity with total wheel time.
This drive requires moderate attention. Across 93.6 miles you will encounter 27 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 14.9 miles (I 90 / Jane Addams Memorial Tollway): Highway fork - watch signs carefully. Lane positioning matters here; at 35.2 miles (I 90 / Jane Addams Memorial Tollway): Highway fork - watch signs carefully. Lane positioning matters here; at 75.8 miles (I 90 / Jane Addams Memorial Tollway): Highway fork - watch signs carefully. 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 1h 58m. Total distance: 93.6 miles.
Family Friendly
Moderate complexity with 0 natural rest stops along the way.
Solo Traveler
1h 58m drive, comfortable solo distance.
Scenic Drive
Mostly surface roads route profile.
Frequently Asked Questions
The longest stretch is about 69.7 miles on Jane Addams Memorial Tollway. The full list of main roads is in the Roads section above.
Expect about $4.84 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.
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 Chicago, IL before sunset when you can. Check the Trip Plan for departure windows that land you in daylight.
Yes. At under 2 hours behind the wheel, this works well for families — plan one quick stop if you have younger kids.
The main spots that need attention: at 14.9 miles (I 90 / Jane Addams Memorial Tollway): Highway fork - watch signs carefully. Lane positioning matters here; at 35.2 miles (I 90 / Jane Addams Memorial Tollway): Highway fork - watch signs carefully. Lane positioning matters here; at 75.8 miles (I 90 / Jane Addams Memorial Tollway): Highway fork - watch signs carefully. Lane positioning matters here.
Yes. A round trip is manageable in a single day if you plan a break at Chicago, IL before heading back.
