Flights from Chicago to Canada from $ 186*

Promotion Code

Changed bag rules and optional services         Cruise Packages

Find United's best fares from Chicago to Canada

$
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  • Chicago (ORD)to

    Edmonton (YEG)
    02/24/26 - 02/28/26
    from
    $ 308
    Viewed: 7 hours ago
    Roundtrip
    Economy

    Chicago (ORD)to

    Winnipeg (YWG)
    02/07/26 - 02/14/26
    from
    $ 629
    Viewed: 6 hours ago
    Roundtrip
    Economy

    Chicago (ORD)to

    Ottawa (YOW)
    01/20/26 - 01/27/26
    from
    $ 682
    Viewed: 7 hours ago
    Roundtrip
    Economy

    Chicago (ORD)to

    Québec (YQB)
    12/31/25 - 01/07/26
    from
    $ 508
    Viewed: 7 hours ago
    Roundtrip
    Economy

  • Chicago (ORD)to

    Halifax (YHZ)
    02/04/26 - 02/08/26
    from
    $ 771
    Viewed: 7 hours ago
    Roundtrip
    Economy

    Chicago (ORD)to

    Victoria (YYJ)
    03/04/26 - 03/18/26
    from
    $ 425
    Viewed: 7 hours ago
    Roundtrip
    Economy

*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.

Business class flights from Chicago to Canada

$

Chicago (ORD)to

Vancouver (YVR)
02/03/26 - 02/06/26

Roundtrip

Business

from
$ 1,176
Viewed: 22 hours ago

Chicago (ORD)to

Toronto (YYZ)
03/10/26 - 03/13/26

Roundtrip

Business

from
$ 775
Viewed: 1 hour ago

Chicago (ORD)to

Calgary (YYC)
02/04/26 - 02/11/26

Roundtrip

Business

from
$ 1,037
Viewed: 5 hours ago

Chicago (ORD)to

Montreal (YUL)
01/22/26 - 01/23/26

Roundtrip

Business

from
$ 543
Viewed: 19 hours ago

Chicago (ORD)to

Winnipeg (YWG)
10/23/26 - 10/29/26

Roundtrip

Business

from
$ 985
Viewed: 1 day ago

Chicago (ORD)to

Edmonton (YEG)
01/07/26 - 01/11/26

Roundtrip

Business

from
$ 978
Viewed: 1 day ago

Chicago (ORD)to

Québec (YQB)
07/21/26 - 07/28/26

Roundtrip

Business

from
$ 897
Viewed: 3 hours ago

Chicago (ORD)to

Ottawa (YOW)
02/06/26 - 02/08/26

Roundtrip

Business

from
$ 1,026
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.