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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 March , April 2026

24 Mar - 30 Apr $ 395.00
YWG
Winnipeg
WestJet
2 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
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16 Mar - 07 Apr $ 745.00
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
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10 Mar - 07 Apr $ 1,064.00
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

10 Mar - 31 Mar $ 838.00
YWG
Winnipeg
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YWG
Winnipeg
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10 Mar - 31 Mar $ 846.00
YWG
Winnipeg
United Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YWG
Winnipeg
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10 Mar - 31 Mar $ 846.00
YWG
Winnipeg
United Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YWG
Winnipeg
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One-way flights to Chicago from Winnipeg

2:00 PM - 2:00 PM
United Airlines
0 Stops
2h 35m
YWG - CHI
$ 348
Kiwi
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6:15 AM - 9:00 AM
WestJet
1 Stops
7h 20m
YWG - CHI
$ 410
Kiwi
Pick dates
2:20 PM - 2:20 PM
United Airlines
0 Stops
2h 25m
YWG - CHI
$ 445
Kiwi
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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.