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 Chicago 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 PD6034
YYZ 11:40
ORD 12:35
1.9h
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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 F91595
ATL 18:23
ORD 19:53
2.5h
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WestJet WS1360
YWG 07:30
ATL 11:46
With stops 3.3h
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Frontier Airlines F92291
ATL 19:02
MDW 20:07
2.1h
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WestJet WS1360
YWG 07:30
ATL 11:46
With stops 3.3h
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Frontier Airlines F92779
ATL 21:17
MDW 22:21
2.1h
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WestJet WS1360
YWG 07:30
ATL 11:46
With stops 3.3h
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Frontier Airlines F93397
ATL 18:23
ORD 19:53
2.5h
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Flair Airlines F8642
YWG 09:25
YYZ 12:55
With stops 2.5h
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Air Canada AC509
YYZ 18:30
ORD 19:30
2.0h
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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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Flair Airlines F8644
YWG 10:20
YYZ 13:55
With stops 2.6h
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American Airlines AA3524
YYZ 07:17
ORD 08:27
2.2h
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Flair Airlines F8644
YWG 10:20
YYZ 13:55
With stops 2.6h
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Air Transat TS7060
YTZ 08:50
MDW 09:40
1.8h
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Flair Airlines F8644
YWG 10:20
YYZ 13:55
With stops 2.6h
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Porter Airlines PD2387
YTZ 09:30
MDW 10:20
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 WS231
YWG 16:55
YYC 18:10
With stops 2.3h
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WestJet WS1610
YYC 09:00
ORD 13:35
3.6h
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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 WS247
YWG 18:55
YYC 20:15
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 09:30
MDW 10:20
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 09:30
MDW 10:20
1.8h
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WestJet WS386
YWG 20:05
YYZ 23:35
With stops 2.5h
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Air Transat TS7060
YTZ 08:50
MDW 09:40
1.8h
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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 09:30
MDW 10:20
1.8h
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Flair Airlines F8857
YWG 21:35
YVR 23:00
With stops 3.4h
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Air Canada AC1048
YVR 09:30
ORD 14:41
4.3h
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Porter Airlines PD428
YWG 20:45
YYZ 00:13
With stops 2.5h
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Porter Airlines PD6073
YYZ 18:15
ORD 19:15
2.0h
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Porter Airlines PD428
YWG 20:45
YYZ 00:13
With stops 2.5h
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Porter Airlines PD2387
YTZ 09:30
MDW 10:20
1.8h
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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 09:30
MDW 10:20
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 09:30
MDW 10:20
1.8h
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WestJet WS386
YWG 20:05
YYZ 23:35
With stops 2.5h
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Air Transat TS7060
YTZ 08:50
MDW 09:40
1.8h
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WestJet WS247
YWG 18:55
YYC 20:15
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 09:30
MDW 10:20
1.8h
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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 WS231
YWG 16:55
YYC 18:10
With stops 2.3h
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WestJet WS1610
YYC 09:00
ORD 13:35
3.6h
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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
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Flair Airlines F8644
YWG 10:20
YYZ 13:55
With stops 2.6h
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American Airlines AA3524
YYZ 07:17
ORD 08:27
2.2h
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Flair Airlines F8644
YWG 10:20
YYZ 13:55
With stops 2.6h
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Air Transat TS7060
YTZ 08:50
MDW 09:40
1.8h
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Flair Airlines F8644
YWG 10:20
YYZ 13:55
With stops 2.6h
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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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Air Canada AC509
YYZ 18:30
ORD 19:30
2.0h
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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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WestJet WS1360
YWG 07:30
ATL 11:46
With stops 3.3h
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Frontier Airlines F91595
ATL 18:23
ORD 19:53
2.5h
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WestJet WS1360
YWG 07:30
ATL 11:46
With stops 3.3h
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Frontier Airlines F92291
ATL 19:02
MDW 20:07
2.1h
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WestJet WS1360
YWG 07:30
ATL 11:46
With stops 3.3h
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Frontier Airlines F92779
ATL 21:17
MDW 22:21
2.1h
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United Airlines UA5639
YWG 14:15
ORD 16:36
Nonstop 2.4h
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Check prices
United Airlines UA5639
YWG 14:15
ORD 16:36
Nonstop 2.4h
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Check prices

Top airlines for flights from Winnipeg to Chicago

Multiple airlines provide flights from Winnipeg to Chicago. The best rated one is Frontier Airlines with an average rating of 10.0.

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Frontier Airlines
Frontier Airlines
User rating: 10.0
WestJet
WestJet
User rating: 10.0

FAQs about flight schedules from Winnipeg to Chicago

  • When are 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 23 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.