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Flight times from Winnipeg to Chicago & schedule

The average flight time from Winnipeg to Chicago is About 2 hours 28 minutes, covering a distance of About 1,154.29km.

Flight duration

About 2 hours 28 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 Chicago O'Hare International Airport.

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Earliest first
Latest first
Westjet WS221
YWG 06:00
YYC 07:15
With stops 2.3h
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Westjet WS1610
YYC 12:00
ORD 16:40
3.7h
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Westjet WS380
YWG 06:15
YYZ 09:45
With stops 2.5h
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Porter Airlines PD2387
YTZ 09:30
MDW 10:20
1.8h
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Delta Air Lines DL3660
YWG 06:40
MSP 08:14
With stops 1.6h
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Delta Air Lines DL4750
MSP 11:30
MDW 13:07
1.6h
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United Airlines UA5747
YWG 07:00
ORD 09:34
Nonstop 2.6h
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Westjet WS223
YWG 07:00
YYC 08:15
With stops 2.3h
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Westjet WS1610
YYC 12:00
ORD 16:40
3.7h
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Air Canada AC258
YWG 08:10
YYZ 11:40
With stops 2.5h
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Air Canada AC509
YYZ 13:55
ORD 14:55
2.0h
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Porter Airlines PD422
YWG 09:20
YYZ 12:45
With stops 2.4h
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Porter Airlines PD6010
YYZ 15:13
ORD 16:18
2.1h
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Porter Airlines PD422
YWG 09:20
YYZ 12:45
With stops 2.4h
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Porter Airlines PD2387
YTZ 09:30
MDW 10:20
1.8h
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Flair Airlines F8642
YWG 09:25
YYZ 12:55
With stops 2.5h
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Porter Airlines PD2387
YTZ 09:30
MDW 10:20
1.8h
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Delta Air Lines DL3871
YWG 12:46
MSP 14:19
With stops 1.6h
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Delta Air Lines DL2130
MSP 18:05
ORD 19:43
1.6h
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United Airlines UA5639
YWG 14:15
ORD 16:36
Nonstop 2.4h
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Westjet WS231
YWG 16:55
YYC 18:10
With stops 2.3h
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Westjet WS1610
YYC 12:00
ORD 16:40
3.7h
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Flair Airlines F8648
YWG 17:10
YYZ 20:40
With stops 2.5h
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Porter Airlines PD2387
YTZ 09:30
MDW 10:20
1.8h
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Westjet WS386
YWG 18:05
YYZ 21:35
With stops 2.5h
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Porter Airlines PD2387
YTZ 09:30
MDW 10:20
1.8h
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Air Transat TS7026
YWG 18:55
YHM 22:09
With stops 2.2h
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Porter Airlines PD2387
YTZ 09:30
MDW 10:20
1.8h
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Air Canada AC270
YWG 19:10
YYZ 22:40
With stops 2.5h
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Air Canada AC507
YYZ 14:00
ORD 15:00
2.0h
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Flair Airlines F8644
YWG 20:10
YYZ 23:40
With stops 2.5h
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Porter Airlines PD2387
YTZ 09:30
MDW 10:20
1.8h
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Air Transat TS7439
YWG 20:45
YYZ 00:10
With stops 2.4h
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Air Canada AC503
YYZ 08:05
ORD 09:00
1.9h
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Air Transat TS7439
YWG 20:45
YYZ 00:10
With stops 2.4h
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Porter Airlines PD2387
YTZ 09:30
MDW 10:20
1.8h
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Air Transat TS7439
YWG 20:45
YYZ 00:10
With stops 2.4h
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Porter Airlines PD2393
YTZ 15:50
MDW 16:40
1.8h
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Westjet WS235
YWG 21:05
YYC 22:20
With stops 2.3h
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Westjet WS1610
YYC 12:00
ORD 16:40
3.7h
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Porter Airlines PD428
YWG 20:50
YYZ 00:15
With stops 2.4h
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Porter Airlines PD2387
YTZ 09:30
MDW 10:20
1.8h
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Porter Airlines PD428
YWG 20:50
YYZ 00:15
With stops 2.4h
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Porter Airlines PD2393
YTZ 15:50
MDW 16:40
1.8h
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Porter Airlines PD428
YWG 20:50
YYZ 00:15
With stops 2.4h
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Air Canada AC511
YYZ 20:00
ORD 21:00
2.0h
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Air Transat TS7439
YWG 20:45
YYZ 00:10
With stops 2.4h
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Air Canada AC503
YYZ 08:05
ORD 09:00
1.9h
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Air Transat TS7439
YWG 20:45
YYZ 00:10
With stops 2.4h
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Porter Airlines PD2387
YTZ 09:30
MDW 10:20
1.8h
See prices and details in the app >>
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Air Transat TS7439
YWG 20:45
YYZ 00:10
With stops 2.4h
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Porter Airlines PD2393
YTZ 15:50
MDW 16:40
1.8h
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Flair Airlines F8644
YWG 20:10
YYZ 23:40
With stops 2.5h
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Porter Airlines PD2387
YTZ 09:30
MDW 10:20
1.8h
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Air Canada AC270
YWG 19:10
YYZ 22:40
With stops 2.5h
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Air Canada AC507
YYZ 14:00
ORD 15:00
2.0h
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Air Transat TS7026
YWG 18:55
YHM 22:09
With stops 2.2h
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Porter Airlines PD2387
YTZ 09:30
MDW 10:20
1.8h
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Westjet WS386
YWG 18:05
YYZ 21:35
With stops 2.5h
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Porter Airlines PD2387
YTZ 09:30
MDW 10:20
1.8h
See prices and details in the app >>
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Flair Airlines F8648
YWG 17:10
YYZ 20:40
With stops 2.5h
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Porter Airlines PD2387
YTZ 09:30
MDW 10:20
1.8h
See prices and details in the app >>
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Westjet WS231
YWG 16:55
YYC 18:10
With stops 2.3h
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Westjet WS1610
YYC 12:00
ORD 16:40
3.7h
See prices and details in the app >>
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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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Delta Air Lines DL3871
YWG 12:46
MSP 14:19
With stops 1.6h
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Delta Air Lines DL2130
MSP 18:05
ORD 19:43
1.6h
See prices and details in the app >>
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Flair Airlines F8642
YWG 09:25
YYZ 12:55
With stops 2.5h
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Porter Airlines PD2387
YTZ 09:30
MDW 10:20
1.8h
See prices and details in the app >>
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Porter Airlines PD422
YWG 09:20
YYZ 12:45
With stops 2.4h
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Porter Airlines PD6010
YYZ 15:13
ORD 16:18
2.1h
See prices and details in the app >>
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Porter Airlines PD422
YWG 09:20
YYZ 12:45
With stops 2.4h
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Porter Airlines PD2387
YTZ 09:30
MDW 10:20
1.8h
See prices and details in the app >>
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Air Canada AC258
YWG 08:10
YYZ 11:40
With stops 2.5h
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Air Canada AC509
YYZ 13:55
ORD 14:55
2.0h
See prices and details in the app >>
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Check prices
United Airlines UA5747
YWG 07:00
ORD 09:34
Nonstop 2.6h
See prices and details in the app >>
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See all
United Airlines UA5747
YWG 07:00
ORD 09:34
Nonstop 2.6h
See prices and details in the app >>
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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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United Airlines UA5639
YWG 14:15
ORD 16:36
Nonstop 2.4h
See prices and details in the app >>
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United Airlines UA5747
YWG 07:00
ORD 09:34
Nonstop 2.6h
See prices and details in the app >>
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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 27 minutes to fly from Winnipeg (YWG) to Chicago (CHI).
  • Airlines with flights from Winnipeg (YWG) to Chicago (CHI): Air Canada, United Airlines, Air New Zealand, avianca and Copa Airlines.

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