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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 August , September 2026

27 Aug - 29 Sep $ 343.00
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
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27 Aug - 02 Sep $ 665.00
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
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27 Aug - 01 Sep $ 901.00
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

27 Aug - 31 Aug $ 657.00
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
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27 Aug - 31 Aug $ 869.00
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
2 STOPS
YWG
Winnipeg
Pick dates
27 Aug - 31 Aug $ 998.00
YWG
Winnipeg
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YWG
Winnipeg
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One-way flights to Chicago from Winnipeg

9:25 AM - 4:00 PM
Air Canada
1 Stops
7h 32m
YWG - CHI
$ 378
Kiwi
Pick dates
9:20 AM - 3:14 PM
Porter Airlines
1 Stops
6h 59m
YWG - CHI
$ 425
Kiwi
Pick dates
2:00 PM - 2:00 PM
Air Canada
0 Stops
2h 35m
YWG - CHI
$ 520
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.