Earn point on your loyalty program!arrow arc left

Cheap flights from Winnipeg (YWG) to Chicago (CHI)

Know your dates, get live prices in seconds
airplane logo

pin logo

calendar
Departure
calendar backward
Return
airplane logo
1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
Save up to 31%
Book Flight + Hotel at the same time

How to find the cheapest flight from Winnipeg (YWG) to Chicago (CHI)

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.
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.

Cheap flights from Winnipeg to Chicago in April , May 2026

22 Apr - 24 May $ 365.00
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
Pick dates
14 Apr - 04 May $ 541.00
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
Pick dates
12 Apr - 05 May $ 951.00
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
Pick dates

Last minute flights from Winnipeg to Chicago

22 Apr - 30 Apr $ 361.00
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
Pick dates
14 Apr - 30 Apr $ 511.00
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
Pick dates
12 Apr - 30 Apr $ 857.00
YWG
Winnipeg
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YWG
Winnipeg
Pick dates

One-way flights to Chicago from Winnipeg

12:10 PM - 6:27 PM
Porter Airlines
1 Stops
7h 22m
YWG - CHI
$ 204
Kiwi
Pick dates
11:55 AM - 6:15 PM
WestJet
1 Stops
7h 57m
YWG - CHI
$ 367
Kiwi
Pick dates
2:00 PM - 2:00 PM
United Airlines
0 Stops
2h 35m
YWG - CHI
$ 443
Kiwi
Pick dates

How to find the cheapest flight from Winnipeg (YWG) to Chicago (CHI)

Related info for your journey
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.
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.