Winnipeg to Chicago Flights from US$119 incl. tax

Discover the best flight deals from Winnipeg to Chicago

Winnipeg to Chicago Flights

Compare and book the best deals

07:30
YWG
Winnipeg
10h 57m
1 stop
18:27
ORD
Chicago
US$293
US$119
59% OFF
07:30
YWG
Winnipeg
14h 47m
1 stop
22:17
MDW
Chicago
US$293
US$124
57% OFF
07:30
YWG
Winnipeg
15h 14m
1 stop
22:44
ORD
Chicago
US$293
US$126
56% OFF
06:15
YWG
Winnipeg
7h 20m
1 stop
13:35
ORD
Chicago
US$293
US$126
56% OFF
07:30
YWG
Winnipeg
14h 51m
1 stop
22:21
MDW
Chicago
US$293
US$129
56% OFF
07:30
YWG
Winnipeg
15h 9m
1 stop
22:39
ORD
Chicago
US$293
US$131
56% OFF

Winnipeg to Chicago Departure Airports

Airports in Winnipeg

Winnipeg to Chicago Airlines

Airlines operating flights on this route