Earn point on your loyalty program!arrow arc left

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

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 Chicago (CHI) to Winnipeg (YWG)

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.
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.

Cheap flights from Chicago to Winnipeg in April , May 2026

30 Apr - 03 May $ 298.00
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
Pick dates
14 Apr - 03 May $ 563.00
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
Pick dates
08 Apr - 08 May $ 794.00
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
Pick dates

Last minute flights from Chicago to Winnipeg

19 Apr - 30 Apr $ 460.00
CHI
Chicago
Sun Country Airlines
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
Sun Country Airlines
2 STOPS
CHI
Chicago
Pick dates
14 Apr - 30 Apr $ 696.00
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
2 STOPS
CHI
Chicago
Pick dates
08 Apr - 30 Apr $ 1,060.00
CHI
Chicago
WestJet
1 STOPS
YWG
Winnipeg
YWG
Winnipeg
WestJet
1 STOPS
CHI
Chicago
Pick dates

One-way flights to Winnipeg from Chicago

5:30 PM - 9:55 PM
WestJet
1 Stops
7h 25m
CHI - YWG
$ 145
Kiwi
Pick dates
6:25 AM - 9:15 AM
WestJet
1 Stops
4h 31m
CHI - YWG
$ 410
Kiwi
Pick dates
9:18 AM - 9:18 AM
United Airlines
0 Stops
2h 34m
CHI - YWG
$ 508
Kiwi
Pick dates

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

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 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.