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Flight times from Winnipeg to Chicago & schedule

The average flight time from Winnipeg to Chicago is About 2 hours 23 minutes, covering a distance of About 1,154.29km.

Flight duration

About 2 hours 23 minutes

Flight distance

About 1,154.29km

How long is the flight from Winnipeg to Chicago?

The flights usually depart from Winnipeg James Armstrong Richardson International Airport and arrive at O'Hare International Airport.

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Earliest first
Latest first
Porter Airlines PD424
YWG 05:00
YYZ 08:33
With stops 2.5h
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Porter Airlines PD6065
YYZ 13:12
ORD 14:12
2.0h
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Westjet WS382
YWG 05:00
YYZ 08:30
With stops 2.5h
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Porter Airlines PD2393
YTZ 13:45
MDW 14:35
1.8h
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Westjet WS223
YWG 07:00
YYC 08:15
With stops 2.3h
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Westjet WS1610
YYC 09:00
ORD 13:35
3.6h
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Westjet WS1360
YWG 07:30
ATL 11:46
With stops 3.3h
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Frontier Airlines F93397
ATL 21:15
ORD 22:39
2.4h
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Westjet WS1360
YWG 07:30
ATL 11:46
With stops 3.3h
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Frontier Airlines F92291
ATL 17:34
MDW 18:37
2.0h
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Westjet WS1360
YWG 07:30
ATL 11:46
With stops 3.3h
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Frontier Airlines F92779
ATL 21:10
MDW 22:14
2.1h
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Westjet WS1360
YWG 07:30
ATL 11:46
With stops 3.3h
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Delta Air Lines DL1076
ATL 20:50
MDW 21:45
1.9h
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Westjet WS1346
YWG 08:00
MCO 13:03
With stops 4.0h
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Spirit Airlines NK393
MCO 17:34
ORD 19:47
3.2h
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Westjet WS1146
YWG 08:00
FLL 13:28
With stops 4.5h
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Frontier Airlines F92206
FLL 17:14
ORD 19:50
3.6h
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Westjet WS384
YWG 12:20
YYZ 15:50
With stops 2.5h
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Porter Airlines PD2387
YTZ 11:20
MDW 12:10
1.8h
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United Airlines UA5639
YWG 14:15
ORD 16:36
Nonstop 2.4h
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Westjet WS229
YWG 14:55
YYC 16:10
With stops 2.3h
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Westjet WS1610
YYC 09:00
ORD 13:35
3.6h
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Westjet WS1396
YWG 16:55
PHX 18:31
With stops 3.6h
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Frontier Airlines F91828
PHX 11:19
ORD 17:00
3.7h
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Westjet WS247
YWG 18:55
YYC 20:11
With stops 2.3h
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Westjet WS1610
YYC 09:00
ORD 13:35
3.6h
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Air Transat TS7439
YWG 18:55
YYZ 22:20
With stops 2.4h
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Porter Airlines PD2387
YTZ 11:20
MDW 12:10
1.8h
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Westjet WS386
YWG 20:05
YYZ 23:35
With stops 2.5h
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Porter Airlines PD2387
YTZ 11:20
MDW 12:10
1.8h
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Westjet WS386
YWG 20:05
YYZ 23:35
With stops 2.5h
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Porter Airlines PD2393
YTZ 13:45
MDW 14:35
1.8h
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Westjet WS386
YWG 20:05
YYZ 23:35
With stops 2.5h
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American Airlines AA3608
YYZ 16:44
ORD 17:44
2.0h
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Flair Airlines F8640
YWG 20:20
YYZ 23:55
With stops 2.6h
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American Airlines AA3524
YYZ 06:15
ORD 07:25
2.2h
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Flair Airlines F8640
YWG 20:20
YYZ 23:55
With stops 2.6h
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Air Canada AC8901
YYZ 08:15
ORD 09:09
1.9h
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Westjet WS251
YWG 21:00
YYC 22:16
With stops 2.3h
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Westjet WS1610
YYC 09:00
ORD 13:35
3.6h
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Porter Airlines PD428
YWG 20:45
YYZ 00:10
With stops 2.4h
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Porter Airlines PD6073
YYZ 18:23
ORD 19:23
2.0h
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Porter Airlines PD428
YWG 20:45
YYZ 00:10
With stops 2.4h
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Porter Airlines PD2387
YTZ 11:20
MDW 12:10
1.8h
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Porter Airlines PD428
YWG 20:45
YYZ 00:10
With stops 2.4h
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Porter Airlines PD2393
YTZ 13:45
MDW 14:35
1.8h
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Flair Airlines F8857
YWG 20:30
YVR 21:55
With stops 3.4h
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Air Canada AC1048
YVR 08:30
ORD 14:41
4.2h
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Flair Airlines F8640
YWG 20:20
YYZ 23:55
With stops 2.6h
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American Airlines AA3524
YYZ 06:15
ORD 07:25
2.2h
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Flair Airlines F8640
YWG 20:20
YYZ 23:55
With stops 2.6h
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Air Canada AC8901
YYZ 08:15
ORD 09:09
1.9h
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Flair Airlines F8640
YWG 20:20
YYZ 23:55
With stops 2.6h
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United Airlines UA2066
YYZ 08:45
ORD 09:50
2.1h
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Flair Airlines F8640
YWG 20:20
YYZ 23:55
With stops 2.6h
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Porter Airlines PD2387
YTZ 11:20
MDW 12:10
1.8h
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Flair Airlines F8640
YWG 20:20
YYZ 23:55
With stops 2.6h
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Air Canada AC507
YYZ 14:00
ORD 14:56
1.9h
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Flair Airlines F8640
YWG 20:20
YYZ 23:55
With stops 2.6h
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Porter Airlines PD2393
YTZ 13:45
MDW 14:35
1.8h
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Flair Airlines F8640
YWG 20:20
YYZ 23:55
With stops 2.6h
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American Airlines AA3608
YYZ 16:44
ORD 17:44
2.0h
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Westjet WS386
YWG 20:05
YYZ 23:35
With stops 2.5h
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Porter Airlines PD2387
YTZ 11:20
MDW 12:10
1.8h
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Westjet WS386
YWG 20:05
YYZ 23:35
With stops 2.5h
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Porter Airlines PD2393
YTZ 13:45
MDW 14:35
1.8h
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Westjet WS386
YWG 20:05
YYZ 23:35
With stops 2.5h
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American Airlines AA3608
YYZ 16:44
ORD 17:44
2.0h
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Westjet WS247
YWG 18:55
YYC 20:11
With stops 2.3h
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Westjet WS1610
YYC 09:00
ORD 13:35
3.6h
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Air Transat TS7439
YWG 18:55
YYZ 22:20
With stops 2.4h
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Porter Airlines PD2387
YTZ 11:20
MDW 12:10
1.8h
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Westjet WS1396
YWG 16:55
PHX 18:31
With stops 3.6h
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Frontier Airlines F91828
PHX 11:19
ORD 17:00
3.7h
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Westjet WS229
YWG 14:55
YYC 16:10
With stops 2.3h
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Westjet WS1610
YYC 09:00
ORD 13:35
3.6h
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United Airlines UA5639
YWG 14:15
ORD 16:36
Nonstop 2.4h
See prices and details in the app >>
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See all
United Airlines UA5639
YWG 14:15
ORD 16:36
Nonstop 2.4h
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United Airlines UA5639
YWG 14:15
ORD 16:36
Nonstop 2.4h
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FAQs about flight schedules from Winnipeg to Chicago

  • When to buy flight tickets from Winnipeg (YWG) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from Winnipeg to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • It takes about 2 hours 21 minutes to fly from Winnipeg (YWG) to Chicago (CHI).
  • Airlines with flights from Winnipeg (YWG) to Chicago (CHI): Air New Zealand, United Airlines, avianca and Air Canada.

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