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Cheap flights from Winnipeg (YWG) to Chicago (CHI)

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1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
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How to find the cheapest flight from Winnipeg (YWG) to Chicago (CHI)

How to find the cheapest flight from Winnipeg (YWG) to Chicago (CHI)
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How to find the cheapest flight from Winnipeg (YWG) to Chicago (CHI)
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How to find the cheapest flight from Winnipeg (YWG) to Chicago (CHI)
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Cheap flights from Winnipeg to Chicago in May , June 2026

31 May - 09 Jun $ 452.00
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
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24 May - 09 Jun $ 546.00
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
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26 May - 05 Jun $ 889.00
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
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Last minute flights from Winnipeg to Chicago

26 May - 01 Jun $ 726.00
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
2 STOPS
YWG
Winnipeg
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28 May - 31 May $ 866.00
YWG
Winnipeg
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YWG
Winnipeg
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26 May - 31 May $ 1,235.00
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
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One-way flights to Chicago from Winnipeg

9:20 AM - 3:10 PM
Porter Airlines
1 Stops
7h
YWG - CHI
$ 236
Kiwi
Pick dates
5:41 PM - 7:45 PM
WestJet
1 Stops
3h 39m
YWG - CHI
$ 396
Kiwi
Pick dates
7:00 AM - 7:00 AM
United Airlines
0 Stops
2h 34m
YWG - CHI
$ 480
Kiwi
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How to find the cheapest flight from Winnipeg (YWG) to Chicago (CHI)

Related info for your journey
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How to find the cheapest flight from Winnipeg (YWG) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Winnipeg (YWG) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.