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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 October , November 2026

30 Oct - 26 Nov $ 655.00
CHI
Chicago
Air Canada
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
Air Canada
1 STOPS
CHI
Chicago
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26 Oct - 02 Nov $ 1,053.00
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
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26 Oct - 10 Nov $ 1,076.00
CHI
Chicago
Air Canada
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
Air Canada
1 STOPS
CHI
Chicago
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Last minute flights from Chicago to Winnipeg

30 Oct - 31 Oct $ 788.00
CHI
Chicago
Air Canada
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
Air Canada
1 STOPS
CHI
Chicago
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26 Oct - 31 Oct $ 1,069.00
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
2 STOPS
CHI
Chicago
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22 Oct - 31 Oct $ 1,514.00
CHI
Chicago
Air Canada
DIRECT
YWG
Winnipeg
YWG
Winnipeg
Air Canada
DIRECT
CHI
Chicago
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One-way flights to Winnipeg from Chicago

8:45 AM - 4:20 PM
Flair Airlines
1 Stops
9h 25m
CHI - YWG
$ 339
Kiwi
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9:59 AM - 3:09 PM
WestJet
1 Stops
6h 51m
CHI - YWG
$ 613
Kiwi
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10:00 AM - 10:00 AM
United Airlines
0 Stops
2h 37m
CHI - YWG
$ 746
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.