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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 August , September 2026

24 Aug - 06 Sep $ 405.00
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
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26 Aug - 10 Sep $ 424.00
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
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18 Aug - 17 Sep $ 1,311.00
CHI
Chicago
United Airlines
DIRECT
YWG
Winnipeg
YWG
Winnipeg
United Airlines
DIRECT
CHI
Chicago
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Last minute flights from Chicago to Winnipeg

25 Aug - 01 Sep $ 570.00
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
2 STOPS
CHI
Chicago
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26 Aug - 31 Aug $ 666.00
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
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21 Aug - 31 Aug $ 1,395.00
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

5:30 PM - 8:10 AM
WestJet
1 Stops
17h 40m
CHI - YWG
$ 195
Kiwi
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5:30 PM - 2:25 PM
WestJet
1 Stops
23h 55m
CHI - YWG
$ 195
Kiwi
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9:15 AM - 9:15 AM
United Airlines
0 Stops
2h 37m
CHI - YWG
$ 584
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.