How far is Winamac, IN from Chicago, IL?
The driving distance from Winamac, IN to Chicago, IL is about 101 miles (162.6 km), with a travel time of about 02h 17m by car.
- The straight-line flight distance is about 77.4 miles (124.5 km).
- For a round trip, plan for roughly 04h 34m of driving time before adding stops, traffic, or weather delays.
- A comfortable departure window is usually 8:00 AM to 10:00 AM EDT.
Reverse, save, or send this route
This route works well as a day trip with time at the destination. Copy the route link, send it to another device, or print a clean version before you head out.
This route works well as a day trip with time at the destination.
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 02h 17m.
A morning start gives you useful time at the destination and keeps the return out of the late evening.
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.
Town in Porter County, Indiana, United States
Route Weather Snapshot
Check the forecast at both ends before you head out.
Sunny
Driving Route Map
The map below follows the saved road route between Winamac and Chicago.
Turn-by-Turn Driving Directions
Step-by-step road directions between Winamac and Chicago.
-
1
Start on North Monticello Street
10.5 mi · 16 min · North Monticello Street
-
2
Continue on S 400 E
1.4 mi · 2 min · S 400 E
-
3
Turn left onto East 600 S
4 mi · 5 min · East 600 S
-
4
Continue on West 600 South
2 mi · 3 min · West 600 South
-
5
Turn right onto S 200 W
8.6 mi · 12 min · S 200 W
-
6
Continue on State Road 39
4.6 mi · 6 min · State Road 39
-
7
Turn left onto Lincoln Highway
15.5 mi · 20 min · Lincoln Highway
-
8
Take the exit slight right toward SR 49 North, SR 2 East: Valparaiso, Chesterton
9.2 mi · 13 min
-
9
Turn left onto I 80, I 90: Toll Road
120 m · 10 sec
-
10
Continue straight
757 ft · 18 sec
-
11
Continue on I 80, I 90: Toll Road
125 m · 10 sec
-
12
Keep slight right to continue on I 80 West, I 90 West: Chicago
1246 ft · 31 sec
-
13
Merge slight left onto Indiana Toll Road
29.4 mi · 33 min · Indiana Toll Road
-
14
Turn straight onto Indiana Toll Road
963 ft · 2 min · Indiana Toll Road
-
15
Merge slight right onto Indiana Toll Road
1.6 km · 2 min · Indiana Toll Road
-
16
Continue on Chicago Skyway
2.9 mi · 5 min · Chicago Skyway
-
17
Turn straight onto Chicago Skyway
724 ft · 18 sec · Chicago Skyway
-
18
Merge slight left onto Chicago Skyway
4.1 mi · 6 min · Chicago Skyway
-
19
Keep slight left to continue on Chicago Skyway
1987 ft · 31 sec · Chicago Skyway
-
20
Merge slight left onto Dan Ryan Expressway (Express)
5.5 mi · 8 min · Dan Ryan Expressway (Express)
-
21
Take the exit slight right toward Canalport Avenue, Cermak Road
1620 ft · 40 sec
-
22
Turn slight left onto South Ruble Street
74 m · 7 sec · South Ruble Street
-
23
Turn slight left
23 m · 5 sec
-
24
Turn left onto South Canalport Avenue
887 ft · 26 sec · South Canalport Avenue
-
25
Turn left onto South Halsted Street
737 ft · 19 sec · South Halsted Street
-
26
Turn right onto West Cermak Road
976 ft · 25 sec · West Cermak Road
-
27
Turn left
46 m · 11 sec
-
28
Turn right
794 ft · 58 sec
-
29
Arrive at your destination
0 m · 1 sec
Car Route Details
A richer read on the saved driving route between Winamac and Chicago.
Turn-heavy local drive
The route has frequent decision points for its length, so lane choice and turn timing will matter more than cruising speed.
Indiana Toll Road
Merge slight left onto Indiana Toll Road
29.4 mi · 00h 33m
Route Summary
A quick read on whether this route feels easy, ambitious, or worth planning around.
A comfortable day-trip route
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
Sunny leaving Winamac and Sunny near Chicago.
Trip Questions
Direct answers travelers usually want before committing to the drive.
How long does it take to drive from Winamac to Chicago?
The road trip is about 101 miles (162.6 km) and usually takes 02h 17m in normal driving conditions.
Is this a same-day trip or an overnight route?
This route works well as a day trip. You can leave in the morning, spend meaningful time at the destination, and still return the same day.
What is the halfway point on this route?
Valparaiso is a useful midpoint, sitting about 50.5 miles from Winamac and 50.6 miles from Chicago.
How much longer is the road route than the straight-line distance?
The direct path is about 77.4 miles (124.5 km), while the road route adds roughly 23.6 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 8:00 AM to 10:00 AM EDT. If you want a more comfortable same-day return, try to leave by 1:56 PM EDT.
How much will gas cost for this route?
Using about 28.3 MPG, regular gas is estimated at $13.91 one way or $27.82 round trip. Estimated CO2 is about 31.6 kg one way.
Do you cross a time zone on this route?
Yes. There is about a 1 hour time difference between Winamac and Chicago, so arrival and return times should be read in local time.
What should you check before leaving?
Before you leave, expect Sunny around Winamac and Sunny near Chicago.
Stop Ideas Near Valparaiso
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 Valparaiso.
Gary, IN
Michigan City
Dyer station
New Buffalo, Michigan
Flight Path Map
This map shows the direct air route between Winamac and Chicago. Straight-line distance: 77.36 mi (124.5 km).
#1 Winamac
County seat in Indiana
| Population | 2,295 |
| Coordinates | 41.0514300, -86.6030600 |
| Altitude | 215 |
| Country | United States |
#2 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 |
End: Chicago (-87.650052, 41.850033)
Estimated Travel Time
Distance: 163 km by road
| Speed | Time |
|---|---|
| 30 mph (48.3 km/h) | 03h 21m |
| 40 mph (64.37 km/h) | 02h 31m |
| 50 mph (80.47 km/h) | 02h 01m |
| 60 mph (96.56 km/h) | 01h 41m |
| 70 mph (112.65 km/h) | 01h 26m |
| 80 mph (129 km/h) | 01h 15m |
Fuel, Round Trip and CO2
Estimated fuel cost and emissions for this route.
| Fuel | $/gal | One way | Round trip |
|---|---|---|---|
| Regular gas | $3.91 | $13.91 | $27.82 |
| Mid-grade | $4.49 | $15.97 | $31.94 |
| Premium | $5.01 | $17.85 | $35.69 |
| Diesel | $6.64 | $23.63 | $47.26 |
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 Indiana · Oct 13, 2026