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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 March , April 2026

25 Mar - 26 Apr $ 335.00
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
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14 Mar - 06 Apr $ 674.00
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
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11 Mar - 08 Apr $ 891.00
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

25 Mar - 01 Apr $ 454.00
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
2 STOPS
CHI
Chicago
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14 Mar - 01 Apr $ 731.00
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
2 STOPS
CHI
Chicago
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11 Mar - 31 Mar $ 1,276.00
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

6:05 AM - 12:40 PM
WestJet
1 Stops
9h 4m
CHI - YWG
$ 175
Kiwi
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6:15 AM - 9:15 AM
WestJet
1 Stops
4h 46m
CHI - YWG
$ 436
Kiwi
Pick dates
9:15 AM - 9:15 AM
United Airlines
0 Stops
2h 42m
CHI - YWG
$ 501
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.