Flights from Calgary to Chicago from $ 314*

Promotion Code

Changed bag rules and optional services         Cruise Packages

Featured daily fares for flights from Calgary (YYC) to Chicago (ORD)

Try alternate month or interact with individual days below in order to find offers.
Mar 2026
No result for this month
Apr 2026
No result for this month
May 2026
From$ 382*
Viewed: 1 day ago
RoundTrip|Economy
Displaying fares for March-2026
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    • *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 Calgary (YYC) to Chicago (ORD) flights

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    More United deals on Calgary (YYC) to Chicago (ORD) flights
    From
    To
    Fare Type
    Dates
    Price
    Calgary (YYC)Chicago (ORD)Roundtrip
    |
    Economy    		06/01/26 - 06/04/26

    from

    $ 314

    Viewed: 1 day ago

    Calgary (YYC)Chicago (ORD)Roundtrip
    |
    Economy    		05/31/26 - 06/04/26

    from

    $ 382

    Viewed: 1 day ago

    Calgary (YYC)Chicago (ORD)Roundtrip
    |
    Economy    		05/08/26 - 05/11/26

    from

    $ 498

    Viewed: 1 day ago

    Calgary (YYC)Chicago (ORD)Roundtrip
    |
    Economy    		06/01/26 - 06/04/26

    from

    $ 563

    Viewed: 1 day ago

    Calgary (YYC)Chicago (ORD)Roundtrip
    |
    Economy    		05/31/26 - 06/04/26

    from

    $ 631

    Viewed: 1 day ago

    Calgary (YYC)Chicago (ORD)Roundtrip
    |
    Economy    		06/01/26 - 06/04/26

    from

    $ 697

    Viewed: 1 day ago

    Calgary (YYC)Chicago (ORD)Roundtrip
    |
    Economy    		05/31/26 - 06/04/26

    from

    $ 711

    Viewed: 1 day ago

    Calgary (YYC)Chicago (ORD)Roundtrip
    |
    Economy    		05/08/26 - 05/11/26

    from

    $ 748

    Viewed: 1 day 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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