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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 July , August 2026

29 Jul - 19 Aug $ 683.00
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
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29 Jul - 09 Aug $ 902.00
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
2 STOPS
YWG
Winnipeg
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29 Jul - 01 Aug $ 1,278.00
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

29 Jul - 31 Jul $ 983.00
YWG
Winnipeg
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YWG
Winnipeg
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29 Jul - 31 Jul $ 1,055.00
YWG
Winnipeg
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YWG
Winnipeg
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29 Jul - 31 Jul $ 1,239.00
YWG
Winnipeg
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YWG
Winnipeg
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One-way flights to Chicago from Winnipeg

3:59 PM - 8:15 PM
WestJet
1 Stops
5h 53m
YWG - CHI
$ 517
Kiwi
Pick dates
7:00 AM - 7:00 AM
United Airlines
0 Stops
2h 34m
YWG - CHI
$ 549
Kiwi
Pick dates
7:00 AM - 7:00 AM
United Airlines
0 Stops
2h 34m
YWG - CHI
$ 549
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.