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

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

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

27 Nov - 16 Dec $ 484.00
CHI
Chicago
Frontier Airlines
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
Frontier Airlines
1 STOPS
CHI
Chicago
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10 Nov - 07 Dec $ 1,016.00
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
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09 Nov - 05 Dec $ 1,448.00
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
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Last minute flights from Chicago to Winnipeg

27 Nov - 01 Dec $ 525.00
CHI
Chicago
Frontier Airlines
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
Frontier Airlines
2 STOPS
CHI
Chicago
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10 Nov - 01 Dec $ 1,040.00
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
2 STOPS
CHI
Chicago
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09 Nov - 30 Nov $ 2,673.00
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
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One-way flights to Winnipeg from Chicago

10:15 AM - 4:20 PM
Flair Airlines
1 Stops
7h 55m
CHI - YWG
$ 279
Kiwi
Pick dates
4:30 PM - 9:55 PM
Air Canada
1 Stops
7h 14m
CHI - YWG
$ 663
Kiwi
Pick dates
12:50 PM - 5:20 PM
Air Canada
1 Stops
6h 19m
CHI - YWG
$ 748
Kiwi
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How to find the cheapest flight from Chicago (CHI) to Winnipeg (YWG)

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