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

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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 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 December 2025 , January 2026

27 Dec - 12 Jan $ 525.00
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
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23 Dec - 09 Jan $ 614.00
CHI
Chicago
WestJet
2 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
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20 Dec - 09 Jan $ 1,306.00
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

28 Dec - 31 Dec $ 755.00
CHI
Chicago
United Airlines
DIRECT
YWG
Winnipeg
YWG
Winnipeg
United Airlines
DIRECT
CHI
Chicago
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23 Dec - 01 Jan $ 961.00
CHI
Chicago
WestJet
2 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
2 STOPS
CHI
Chicago
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20 Dec - 31 Dec $ 1,496.00
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

9:10 AM - 9:10 AM
United Airlines
0 Stops
2h 47m
CHI - YWG
$ 353
Kiwi
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10:50 AM - 10:10 PM
United Airlines
2 Stops
13h 4m
CHI - YWG
$ 475
Kiwi
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9:22 AM - 9:22 AM
United Airlines
0 Stops
2h 35m
CHI - YWG
$ 602
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.