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Winnipeg, MB, Canada (YWG) to Chicago, IL, United States (ORD)

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Showing the top 50 roundtrips of 79 results Show all 79

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Roundtrip: £870.10

06:00 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 08:11

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 5945
	Direct flight

09:50 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 16:05

Thu 20-Jun
Duration: 6hr 15mn

	WestJet 5638 / 697
	Connect in Montreal (YUL)

Select this flight

Roundtrip: £872.90

06:00 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 08:11

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 5945
	Direct flight

09:50 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 18:19

Thu 20-Jun
Duration: 8hr 29mn

	WestJet 5638 / 589 / 525
	Connect in Montreal (YUL), Toronto (YYZ)

Select this flight

Roundtrip: £872.90

06:00 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 08:11

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 5945
	Direct flight

09:50 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 19:34

Thu 20-Jun
Duration: 9hr 44mn

	WestJet 5638 / 589 / 301
	Connect in Montreal (YUL), Toronto (YYZ)

Select this flight

Roundtrip: £872.90

06:00 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 08:11

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 5945
	Direct flight

09:50 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 19:34

Thu 20-Jun
Duration: 9hr 44mn

	WestJet 5638 / 591 / 301
	Connect in Montreal (YUL), Toronto (YYZ)

Select this flight

Roundtrip: £889.10

10:00 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 18:05

Thu 20-Jun
Duration: 8hr 5mn

	WestJet 318 / 5650
	Connect in Montreal (YUL)

20:10 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 22:21

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 3813
	Direct flight

Select this flight

Roundtrip: £891.10

07:40 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 11:32

Thu 20-Jun
Duration: 3hr 52mn

	Delta 4736 / 2455
	Connect in Minneapolis (Minneapolis - St. Paul Intl.)

13:40 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 19:34

Thu 20-Jun
Duration: 5hr 54mn

	WestJet 5501 / 301
	Connect in Toronto (YYZ)

Select this flight

Roundtrip: £891.10

07:40 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 11:32

Thu 20-Jun
Duration: 3hr 52mn

	Delta 4736 / 2455
	Connect in Minneapolis (Minneapolis - St. Paul Intl.)

17:20 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 23:19

Thu 20-Jun
Duration: 5hr 59mn

	WestJet 5503 / 535
	Connect in Toronto (YYZ)

Select this flight

Roundtrip: £891.10

10:57 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 16:22

Thu 20-Jun
Duration: 5hr 25mn

	Delta 4809 / 2427
	Connect in Minneapolis (Minneapolis - St. Paul Intl.)

17:20 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 23:19

Thu 20-Jun
Duration: 5hr 59mn

	WestJet 5503 / 535
	Connect in Toronto (YYZ)

Select this flight

Roundtrip: £891.90

09:00 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 18:05

Thu 20-Jun
Duration: 9hr 5mn

	WestJet 528 / 588 / 5650
	Connect in Toronto (YYZ), Montreal (YUL)

20:10 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 22:21

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 3813
	Direct flight

Select this flight

Roundtrip: £891.90

05:25 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 14:55

Thu 20-Jun
Duration: 9hr 30mn

	WestJet 518 / 582 / 5638
	Connect in Toronto (YYZ), Montreal (YUL)

17:47 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 19:58

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 5942
	Direct flight

Select this flight

Roundtrip: £891.90

05:25 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 14:55

Thu 20-Jun
Duration: 9hr 30mn

	WestJet 518 / 582 / 5638
	Connect in Toronto (YYZ), Montreal (YUL)

20:10 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 22:21

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 3813
	Direct flight

Select this flight

Roundtrip: £891.90

05:25 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 18:05

Thu 20-Jun
Duration: 12hr 40mn

	WestJet 518 / 586 / 5650
	Connect in Toronto (YYZ), Montreal (YUL)

20:10 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 22:21

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 3813
	Direct flight

Select this flight

Roundtrip: £895.80

06:00 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 08:11

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 5945
	Direct flight

13:40 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 19:34

Thu 20-Jun
Duration: 5hr 54mn

	WestJet 5501 / 301
	Connect in Toronto (YYZ)

Select this flight

Roundtrip: £895.80

07:20 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 09:31

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 3831
	Direct flight

13:40 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 19:34

Thu 20-Jun
Duration: 5hr 54mn

	WestJet 5501 / 301
	Connect in Toronto (YYZ)

Select this flight

Roundtrip: £895.80

12:26 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 14:34

Thu 20-Jun
Duration: 2hr 8mn

	UNITED 5930
	Direct flight

17:20 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 23:19

Thu 20-Jun
Duration: 5hr 59mn

	WestJet 5503 / 535
	Connect in Toronto (YYZ)

Select this flight

Roundtrip: £895.80

06:00 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 08:11

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 5945
	Direct flight

17:20 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 23:19

Thu 20-Jun
Duration: 5hr 59mn

	WestJet 5503 / 535
	Connect in Toronto (YYZ)

Select this flight

Roundtrip: £895.80

07:20 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 09:31

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 3831
	Direct flight

17:20 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 23:19

Thu 20-Jun
Duration: 5hr 59mn

	WestJet 5503 / 535
	Connect in Toronto (YYZ)

Select this flight

Roundtrip: £895.80

06:00 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 08:11

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 5945
	Direct flight

11:15 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 18:19

Thu 20-Jun
Duration: 7hr 4mn

	WestJet 5657 / 525
	Connect in Toronto (YYZ)

Select this flight

Roundtrip: £895.80

07:20 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 09:31

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 3831
	Direct flight

11:15 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 18:19

Thu 20-Jun
Duration: 7hr 4mn

	WestJet 5657 / 525
	Connect in Toronto (YYZ)

Select this flight

Roundtrip: £983.80

06:00 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 08:11

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 5945
	Direct flight

09:30 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 18:19

Thu 20-Jun
Duration: 8hr 49mn

	American Airlines 384 / 3313 / 8147
	Connect in New York (LGA), Toronto (YYZ)

Select this flight

Roundtrip: £991.70

07:40 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 11:32

Thu 20-Jun
Duration: 3hr 52mn

	Delta 4736 / 2455
	Connect in Minneapolis (Minneapolis - St. Paul Intl.)

15:10 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 00:31 +1 day

Thu 20-Jun
Duration: 9hr 21mn

	American Airlines 360
	UNITED 8429 / 8645
	Connect in New York (LGA), Toronto (YYZ)

Select this flight

Roundtrip: £991.70

07:40 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 11:32

Thu 20-Jun
Duration: 3hr 52mn

	Delta 4736 / 2455
	Connect in Minneapolis (Minneapolis - St. Paul Intl.)

15:10 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 00:31 +1 day

Thu 20-Jun
Duration: 9hr 21mn

	American Airlines 360
	Air Canada 725 / 273
	Connect in New York (LGA), Toronto (YYZ)

Select this flight

Roundtrip: £1,052.00

06:00 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 08:11

Thu 20-Jun
Duration: 2hr 11mn

	Air Canada 3506
	Direct flight

09:30 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 18:01

Thu 20-Jun
Duration: 8hr 31mn

	American Airlines 384
	Air Canada 713 / 267
	Connect in New York (LGA), Toronto (YYZ)

Select this flight

Roundtrip: £1,052.00

06:00 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 08:11

Thu 20-Jun
Duration: 2hr 11mn

	Air Canada 3506
	Direct flight

09:30 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 18:01

Thu 20-Jun
Duration: 8hr 31mn

	American Airlines 384
	UNITED 8447 / 8641
	Connect in New York (LGA), Toronto (YYZ)

Select this flight

Roundtrip: £1,052.00

06:00 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 08:11

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 5945
	Direct flight

09:30 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 18:01

Thu 20-Jun
Duration: 8hr 31mn

	American Airlines 384
	UNITED 8447 / 8641
	Connect in New York (LGA), Toronto (YYZ)

Select this flight

Roundtrip: £1,052.00

06:00 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 08:11

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 5945
	Direct flight

09:30 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 18:01

Thu 20-Jun
Duration: 8hr 31mn

	American Airlines 384
	Air Canada 713 / 267
	Connect in New York (LGA), Toronto (YYZ)

Select this flight

Roundtrip: £1,055.20

05:20 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 17:10

Thu 20-Jun
Duration: 11hr 50mn

	UNITED 8444 / 3870
	American Airlines 3694
	Connect in Toronto (YYZ), Newark (EWR)

20:10 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 22:21

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 3813
	Direct flight

Select this flight

Roundtrip: £1,055.20

05:20 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 17:10

Thu 20-Jun
Duration: 11hr 50mn

	UNITED 8444 / 3870
	American Airlines 3694
	Connect in Toronto (YYZ), Newark (EWR)

20:10 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 22:21

Thu 20-Jun
Duration: 2hr 11mn

	Air Canada 3593
	Direct flight

Select this flight

Roundtrip: £1,055.20

05:20 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 17:10

Thu 20-Jun
Duration: 11hr 50mn

	UNITED 8444 / 3860
	American Airlines 3694
	Connect in Toronto (YYZ), Newark (EWR)

20:10 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 22:21

Thu 20-Jun
Duration: 2hr 11mn

	Air Canada 3593
	Direct flight

Select this flight

Roundtrip: £1,055.20

05:20 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 17:10

Thu 20-Jun
Duration: 11hr 50mn

	UNITED 8444 / 3860
	American Airlines 3694
	Connect in Toronto (YYZ), Newark (EWR)

20:10 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 22:21

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 3813
	Direct flight

Select this flight

Roundtrip: £1,063.60

05:20 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 14:55

Thu 20-Jun
Duration: 9hr 35mn

	Air Canada 256 / 706
	American Airlines 331
	Connect in Toronto (YYZ), New York (LGA)

20:10 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 22:21

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 3813
	Direct flight

Select this flight

Roundtrip: £1,063.60

05:20 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 14:55

Thu 20-Jun
Duration: 9hr 35mn

	Air Canada 256 / 706
	American Airlines 331
	Connect in Toronto (YYZ), New York (LGA)

17:47 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 19:58

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 5942
	Direct flight

Select this flight

Roundtrip: £1,063.60

05:20 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 14:55

Thu 20-Jun
Duration: 9hr 35mn

	Air Canada 256 / 706
	American Airlines 331
	Connect in Toronto (YYZ), New York (LGA)

20:10 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 22:21

Thu 20-Jun
Duration: 2hr 11mn

	Air Canada 3593
	Direct flight

Select this flight

Roundtrip: £1,124.00

06:00 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 08:11

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 5945
	Direct flight

10:57 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 16:51

Thu 20-Jun
Duration: 5hr 54mn

	Air Canada 4994 / 263
	Connect in Toronto (YYZ)

Select this flight

Roundtrip: £1,124.00

06:00 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 08:11

Thu 20-Jun
Duration: 2hr 11mn

	Air Canada 3506
	Direct flight

10:57 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 16:51

Thu 20-Jun
Duration: 5hr 54mn

	Air Canada 4994 / 263
	Connect in Toronto (YYZ)

Select this flight

Roundtrip: £1,124.00

07:20 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 09:31

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 3831
	Direct flight

10:57 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 16:51

Thu 20-Jun
Duration: 5hr 54mn

	Air Canada 4994 / 263
	Connect in Toronto (YYZ)

Select this flight

Roundtrip: £1,124.00

07:20 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 09:31

Thu 20-Jun
Duration: 2hr 11mn

	Air Canada 3197
	Direct flight

10:57 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 16:51

Thu 20-Jun
Duration: 5hr 54mn

	Air Canada 4994 / 263
	Connect in Toronto (YYZ)

Select this flight

Roundtrip: £1,133.80

07:40 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 11:32

Thu 20-Jun
Duration: 3hr 52mn

	Delta 4736 / 2455
	Connect in Minneapolis (Minneapolis - St. Paul Intl.)

15:07 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 19:05

Thu 20-Jun
Duration: 3hr 58mn

	Delta 2186 / 4492
	Connect in Minneapolis (Minneapolis - St. Paul Intl.)

Select this flight

Roundtrip: £1,138.50

07:40 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 11:32

Thu 20-Jun
Duration: 3hr 52mn

	Delta 4736 / 2455
	Connect in Minneapolis (Minneapolis - St. Paul Intl.)

20:10 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 22:21

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 3813
	Direct flight

Select this flight

Roundtrip: £1,138.50

07:40 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 11:32

Thu 20-Jun
Duration: 3hr 52mn

	Delta 4736 / 2455
	Connect in Minneapolis (Minneapolis - St. Paul Intl.)

17:47 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 19:58

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 5942
	Direct flight

Select this flight

Roundtrip: £1,138.50

07:40 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 11:32

Thu 20-Jun
Duration: 3hr 52mn

	Delta 4736 / 2455
	Connect in Minneapolis (Minneapolis - St. Paul Intl.)

15:04 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 17:15

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 5952
	Direct flight

Select this flight

Roundtrip: £1,138.50

10:57 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 16:22

Thu 20-Jun
Duration: 5hr 25mn

	Delta 4809 / 2427
	Connect in Minneapolis (Minneapolis - St. Paul Intl.)

17:47 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 19:58

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 5942
	Direct flight

Select this flight

Roundtrip: £1,143.20

12:26 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 14:34

Thu 20-Jun
Duration: 2hr 8mn

	UNITED 5930
	Direct flight

20:10 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 22:21

Thu 20-Jun
Duration: 2hr 11mn

	Air Canada 3593
	Direct flight

Select this flight

Roundtrip: £1,143.20

12:26 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 14:34

Thu 20-Jun
Duration: 2hr 8mn

	UNITED 5930
	Direct flight

17:47 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 19:58

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 5942
	Direct flight

Select this flight

Roundtrip: £1,143.20

12:26 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 14:34

Thu 20-Jun
Duration: 2hr 8mn

	Air Canada 4659
	Direct flight

17:47 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 19:58

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 5942
	Direct flight

Select this flight

Roundtrip: £1,143.20

12:26 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 14:34

Thu 20-Jun
Duration: 2hr 8mn

	UNITED 5930
	Direct flight

20:10 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 22:21

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 3813
	Direct flight

Select this flight

Roundtrip: £1,143.20

12:26 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 14:34

Thu 20-Jun
Duration: 2hr 8mn

	Air Canada 4659
	Direct flight

20:10 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 22:21

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 3813
	Direct flight

Select this flight

Roundtrip: £1,143.20

14:27 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 16:35

Thu 20-Jun
Duration: 2hr 8mn

	UNITED 5970
	Direct flight

20:10 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 22:21

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 3813
	Direct flight

Select this flight

Roundtrip: £1,143.20

14:27 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 16:35

Thu 20-Jun
Duration: 2hr 8mn

	UNITED 5970
	Direct flight

17:47 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 19:58

Thu 20-Jun
Duration: 2hr 11mn

	UNITED 5942
	Direct flight

Select this flight

Roundtrip: £1,143.20

14:27 Depart Winnipeg (YWG)
Arrive Chicago (ORD) 16:35

Thu 20-Jun
Duration: 2hr 8mn

	UNITED 5970
	Direct flight

20:10 Depart Chicago (ORD)
Arrive Winnipeg (YWG) 22:21

Thu 20-Jun
Duration: 2hr 11mn

	Air Canada 3593
	Direct flight

Select this flight

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