How far is Chicago, IL from Winamac, IN?

The driving distance from Chicago, IL to Winamac, IN is about 100.4 miles (161.6 km), with a travel time of about 02h 18m by car.

  • The straight-line flight distance is about 77.4 miles (124.5 km).
  • For a round trip, plan for roughly 04h 36m of driving time before adding stops, traffic, or weather delays.
  • A comfortable departure window is usually 8:00 AM to 10:00 AM CDT.
Trip Tools

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.

Reverse Route
Quick Snapshot
Road
100.44 mi
02h 18m
Flight
77.36 mi
124.5 km direct

This route works well as a day trip with time at the destination.

Learn Distance

Choose another destination from Chicago.

Flight Distance

Direct air line
77.36 mi
Kilometers
124.5 km
Flight Time
00h 09m

Driving Distance

Road route
100.44 mi
Kilometers
161.65 km
Drive Time
02h 18m

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 18m.

Arrival Snapshot
Arrive in Winamac
Tue, Oct 13, 8:10 PM EDT
Return by in Chicago
Tue, Oct 13, 9:28 PM CDT
Useful when you're deciding between a quick errand, a day trip, or a longer stop.
Leave Chicago
2026-10-13T16:52
Arrive Winamac
Tue, Oct 13, 7:10 PM CDT
Route Timing
02h 18m
One way by road
Best Departure Window
8:00 AM to 10:00 AM CDT
Aim for a morning departure
Arrive between
11:18 AM to 1:18 PM EDT

A morning start gives you useful time at the destination and keeps the return out of the late evening.

Leave by
1:54 PM CDT
Keeps a same-day return open with about 03h 00m at the destination.
Back in Chicago
9:30 PM CDT
Morning start is best

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.

Mid-route stop
Valparaiso
IN

Town in Porter County, Indiana, United States

From Chicago
50.2 mi
01h 09m
To Winamac
50.3 mi
01h 09m

Route Weather Snapshot

Check the forecast at both ends before you head out.

Origin
83°F
Tuesday

Sunny

Starts
Tue, Oct 13 6:00 AM CDT
Wind
10 to 15 mph W
Destination
88°F
Tuesday

Sunny

Starts
Tue, Oct 13 6:00 AM EDT
Wind
10 to 15 mph SW

Driving Route Map

The map below follows the saved road route between Chicago and Winamac.

Turn-by-Turn Driving Directions

Step-by-step road directions between Chicago and Winamac.

  1. 1

    Start on the route

    943 ft · 1 min

  2. 2

    At the end of the road, turn right onto West Cermak Road

    947 ft · 26 sec · West Cermak Road

  3. 3

    Turn left onto South Halsted Street

    737 ft · 17 sec · South Halsted Street

  4. 4

    Turn right onto South Canalport Avenue

    87 m · 6 sec · South Canalport Avenue

  5. 5

    Turn slight right

    34 m · 5 sec

  6. 6

    Take the ramp straight toward I 90 East, I 94 East

    139 m · 11 sec

  7. 7

    Keep slight left to continue on I 90, I 94 East: Indiana

    929 ft · 23 sec

  8. 8

    Merge slight left onto Dan Ryan Expressway

    1.2 km · 48 sec · Dan Ryan Expressway

  9. 9

    Keep slight left to continue on Dan Ryan Expressway (Express)

    3.8 mi · 5 min · Dan Ryan Expressway (Express)

  10. 10

    Take the exit slight right toward I 90 East

    2183 ft · 53 sec

  11. 11

    Merge slight right onto Dan Ryan Expressway (Local)

    2612 ft · 50 sec · Dan Ryan Expressway (Local)

  12. 12

    Keep slight left to continue on Chicago Skyway

    4.5 mi · 7 min · Chicago Skyway

  13. 13

    Turn straight onto Chicago Skyway

    591 ft · 14 sec · Chicago Skyway

  14. 14

    Merge slight left onto Chicago Skyway

    3.1 mi · 5 min · Chicago Skyway

  15. 15

    Continue on Indiana Toll Road

    1.6 km · 2 min · Indiana Toll Road

  16. 16

    Turn straight onto Indiana Toll Road

    961 ft · 2 min · Indiana Toll Road

  17. 17

    Merge slight right onto Indiana Toll Road

    1.8 mi · 2 min · Indiana Toll Road

  18. 18

    Keep slight left to continue on Indiana Toll Road

    27.5 mi · 31 min · Indiana Toll Road

  19. 19

    Take the exit slight right toward SR 49: Chesterton, Valparaiso

    1.2 km · 2 min

  20. 20

    Turn right

    9 mi · 12 min

  21. 21

    Take the exit slight right toward US 30 East: Plymouth

    1548 ft · 39 sec

  22. 22

    Merge slight left onto East Morthland Drive

    21.6 mi · 28 min · East Morthland Drive

  23. 23

    Take the exit slight right

    949 ft · 26 sec

  24. 24

    Keep slight right

    740 ft · 20 sec

  25. 25

    Turn straight onto North 400 East

    6.2 mi · 9 min · North 400 East

  26. 26

    Continue on North Heaton Street

    2.1 mi · 4 min · North Heaton Street

  27. 27

    Continue on South 400 E

    3.9 mi · 5 min · South 400 E

  28. 28

    Continue on S 400 E

    1.4 mi · 2 min · S 400 E

  29. 29

    Continue on South 400 East

    10.5 mi · 16 min · South 400 East

  30. 30

    Arrive at your destination

    0 m · 1 sec · North Monticello Street

Car Route Details

A richer read on the saved driving route between Chicago and Winamac.

OSRM road route
Drive Character

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.

Directions
30 steps
8 turns on the saved route
Ramps & Exits
10
5 merges, 5 ramps or exits
Navigation Density
29.9 / 100 mi
Decision points by distance
Main Roads
Indiana Toll Road
30.5 mi · 30%
East Morthland Drive
21.9 mi · 22%
South 400 East
10.5 mi · 10%
Chicago Skyway
7.71 mi · 8%
North 400 East
6.21 mi · 6%
South 400 E
3.85 mi · 4%
Longest Stretch

Indiana Toll Road

Keep slight left to continue on Indiana Toll Road

27.5 mi · 00h 31m

Route Summary

A quick read on whether this route feels easy, ambitious, or worth planning around.

Trip Read

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.

Drive Time
02h 18m
Day trip friendly
Same-Day Return
04h 36m
Round-trip wheel time
Road vs Air
+23 mi
77.4 mi direct line
Halfway Stop
Valparaiso
01h 09m from Chicago
Leave By
1:54 PM CDT
Morning start is best
Weather Watch

Sunny leaving Chicago and Sunny near Winamac.

Trip Questions

Direct answers travelers usually want before committing to the drive.

How long does it take to drive from Chicago to Winamac?

The road trip is about 100.4 miles (161.6 km) and usually takes 02h 18m 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 50.2 miles from Chicago and 50.3 miles from Winamac.

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 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 CDT. If you want a more comfortable same-day return, try to leave by 1:54 PM CDT.

How much will gas cost for this route?

Using about 28.3 MPG, regular gas is estimated at $16.67 one way or $33.35 round trip. Estimated CO2 is about 31.5 kg one way.

Do you cross a time zone on this route?

Yes. There is about a 1 hour time difference between Chicago and Winamac, so arrival and return times should be read in local time.

What should you check before leaving?

Before you leave, expect Sunny around Chicago and Sunny near Winamac.

Stop Ideas Near Valparaiso

Useful break, food, and waypoint ideas within about 15 miles of the route midpoint.

Mid-route Guidance
Local place coverage is thin around Valparaiso, so nearby transit and meeting points are shown instead.
Reviewed stop coverage is still thin around this midpoint, so practical transit waypoints are shown on the right.

Transit and Meeting Points

Useful pickup, handoff, or rendezvous points close to Valparaiso.

BUS

Gary, IN

27 mi away
100 West 4th Avenue
RAIL

Michigan City

30 mi away
100 Washington St.
RAIL

Dyer station

38 mi away
913 Sheffield Avenue
RAIL

New Buffalo, Michigan

44 mi away
517 South Whittaker Street

Flight Path Map

This map shows the direct air route between Chicago and Winamac. Straight-line distance: 77.36 mi (124.5 km).

Chicago

#1 Chicago

The third most populous city in the United States and the center of the Chicago metropolitan area.

Population2,677,643
Coordinates41.850033, -87.6500523
Altitude179
CountryUnited States
Winamac

#2 Winamac

County seat in Indiana

Population2,295
Coordinates41.0514300, -86.6030600
Altitude215
CountryUnited States
Start: Chicago (-87.650052, 41.850033)
End: Winamac (-86.60306, 41.05143)

Estimated Travel Time

Distance: 162 km by road

SpeedTime
30 mph (48.3 km/h)03h 20m
40 mph (64.37 km/h)02h 30m
50 mph (80.47 km/h)02h 00m
60 mph (96.56 km/h)01h 40m
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.

One-way fuel
3.55 gal
13.42 L · about $16.67
Round trip
$33.35
7.1 gal · 26.84 L
Estimated CO2
31.5 kg one way
Round trip: 63.1 kg / 139 lb CO2, using regular gasoline.
Fuel$/galOne wayRound trip
Regular gas $4.70 $16.67 $33.35
Mid-grade $5.32 $18.89 $37.78
Premium $5.87 $20.83 $41.66
Diesel $6.58 $23.35 $46.70

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 Illinois · Oct 13, 2026

Please keep in mind that there is a 1 hour time gap between Chicago, IL and Winamac, IN. The current time in Chicago is 16:52:44, although it is 17:52:44 in Winamac.

Distance to Other Cities

How did we calculate? Place names are translated into coordinates. The Haversine formula calculates straight-line distance; driving distance uses road network data.