Travel with Air Canada from Chicago to Winnipeg (ORD - YWG) from CAD 379*

*Fares displayed have been collected within the last 48 hours and may no longer be available at the time of booking. Learn more about this offer. Additional baggage fees and charges for optional products and services may apply.

Flights between Chicago and Winnipeg - our lowest fares in cash

Aug 2025
FromUSD 549*
One way/Economy
Sep 2025
FromUSD 215*
One way/Economy
Oct 2025
FromUSD 215*
One way/Economy
USD 215
USD 549
Displaying fares for August-2025
  • 31

    Su

    AUG

  • 08

    Mo

  • 01

    We

    OCT

  • 19

    We

  • 07

    Su

  • 01

    Th

    JAN

  • 02

    Mo

  • 18

    We

  • 09

    Th

  • 21

    Th

  • 05

    Fr

  • 10

    Fr

    • RangeUSD 215-USD 549

    *Fares displayed have been collected within the last 48 hours and may no longer be available at the time of booking. Learn more about this offer. Additional baggage fees and charges for optional products and services may apply.

    Explore all routes from Chicago to Winnipeg