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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 November , December 2026

27 Nov - 11 Dec $ 551.00
YWG
Winnipeg
Flair Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Flair Airlines
1 STOPS
YWG
Winnipeg
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18 Nov - 05 Dec $ 705.00
YWG
Winnipeg
WestJet
2 STOPS
CHI
Chicago
CHI
Chicago
WestJet
2 STOPS
YWG
Winnipeg
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14 Nov - 05 Dec $ 867.00
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 Nov - 30 Nov $ 572.00
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
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17 Nov - 01 Dec $ 856.00
YWG
Winnipeg
Air Canada
2 STOPS
CHI
Chicago
CHI
Chicago
Air Canada
1 STOPS
YWG
Winnipeg
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14 Nov - 30 Nov $ 1,076.00
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

11:00 AM - 4:30 PM
Air Canada
1 Stops
7h 43m
YWG - CHI
$ 310
Kiwi
Pick dates
9:35 PM - 9:15 AM
WestJet
2 Stops
13h 50m
YWG - CHI
$ 462
Kiwi
Pick dates
5:45 PM - 7:54 PM
WestJet
1 Stops
4h 48m
YWG - CHI
$ 592
Kiwi
Pick dates

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.