Flights from Winnipeg to Chicago from $ 698*

Promotion Code

Changed bag rules and optional services         Cruise Packages

Featured daily fares for flights from Winnipeg (YWG) to Chicago (ORD)

May 2026
From$ 913*
Viewed: 6 hours ago
RoundTrip|Economy
Jun 2026
From$ 734*
Viewed: 2 hours ago
RoundTrip|Economy
Jul 2026
No result for this month
cmp-daily-histogram-bars-legend-min-price-aria-label $ 734
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    • Range$ 734-$ 913

    *Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply. Schedules are subject to change without notice.

    More United deals on Winnipeg (YWG) to Chicago (ORD) flights

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    More United deals on Winnipeg (YWG) to Chicago (ORD) flights
    From
    To
    Fare Type
    Dates
    Price
    Winnipeg (YWG)Chicago (ORD)Roundtrip
    |
    Economy    		11/01/26 - 11/07/26

    from

    $ 698

    Viewed: 1 day ago

    Winnipeg (YWG)Chicago (ORD)Roundtrip
    |
    Economy    		11/01/26 - 11/07/26

    from

    $ 739

    Viewed: 1 day ago

    Winnipeg (YWG)Chicago (ORD)Roundtrip
    |
    Economy    		11/01/26 - 11/07/26

    from

    $ 911

    Viewed: 1 day ago

    Winnipeg (YWG)Chicago (ORD)Roundtrip
    |
    Economy    		06/02/26 - 06/03/26

    from

    $ 734

    Viewed: 2 hours ago

    Winnipeg (YWG)Chicago (ORD)Roundtrip
    |
    Economy    		06/02/26 - 06/03/26

    from

    $ 792

    Viewed: 2 hours ago

    Winnipeg (YWG)Chicago (ORD)Roundtrip
    |
    Economy    		05/14/26 - 05/21/26

    from

    $ 913

    Viewed: 6 hours ago

    *Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply. Schedules are subject to change without notice.

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