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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 June , July 2026

19 Jun - 04 Jul $ 641.00
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
Pick dates
30 Jun - 07 Jul $ 727.00
YWG
Winnipeg
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YWG
Winnipeg
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19 Jun - 03 Jul $ 780.00
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

25 Jun - 30 Jun $ 800.00
YWG
Winnipeg
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YWG
Winnipeg
Pick dates
19 Jun - 30 Jun $ 807.00
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
2 STOPS
YWG
Winnipeg
Pick dates
19 Jun - 30 Jun $ 852.00
YWG
Winnipeg
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YWG
Winnipeg
Pick dates

One-way flights to Chicago from Winnipeg

9:20 AM - 3:13 PM
Porter Airlines
1 Stops
6h 58m
YWG - CHI
$ 255
Kiwi
Pick dates
9:20 AM - 3:13 PM
Porter Airlines
1 Stops
6h 58m
YWG - CHI
$ 367
Kiwi
Pick dates
12:56 PM - 12:56 PM
United Airlines
0 Stops
2h 34m
YWG - CHI
$ 482
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.