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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 October , November 2026

31 Oct - 27 Nov $ 708.00
YWG
Winnipeg
Flair Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Flair Airlines
1 STOPS
YWG
Winnipeg
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28 Oct - 10 Nov $ 920.00
YWG
Winnipeg
Air Canada
2 STOPS
CHI
Chicago
CHI
Chicago
Air Canada
1 STOPS
YWG
Winnipeg
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24 Oct - 10 Nov $ 1,118.00
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

29 Oct - 01 Nov $ 786.00
YWG
Winnipeg
Flair Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Flair Airlines
1 STOPS
YWG
Winnipeg
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26 Oct - 31 Oct $ 1,118.00
YWG
Winnipeg
United Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
United Airlines
1 STOPS
YWG
Winnipeg
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22 Oct - 31 Oct $ 1,231.00
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

2:15 PM - 2:15 PM
Air Canada
0 Stops
2h 35m
YWG - CHI
$ 534
Kiwi
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5:15 AM - 1:10 PM
Air Canada
2 Stops
9h 37m
YWG - CHI
$ 540
Kiwi
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2:00 PM - 2:00 PM
Air Canada
0 Stops
2h 35m
YWG - CHI
$ 602
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.