Compare Chicago to Canada flight deals starting at $237

Select journey type

Enter to select travel class and passengers

Find flights from Chicago (ORD) to Canada

Chicago (ORD) to Toronto (YYZ)

Depart Thu 29 Nov 2018,
Return Fri 14 Dec 2018
from$ 237*Viewed: 39 minutes ago

Chicago (ORD) to Vancouver (YVR)

Depart Tue 4 Dec 2018,
Return Wed 19 Dec 2018
from$ 356*Viewed: 39 minutes ago

Chicago (ORD) to Calgary (YYC)

Depart Sat 1 Dec 2018,
Return Sun 16 Dec 2018
from$ 627*Viewed: 39 minutes ago

Chicago (ORD) to Montreal (YUL)

Depart Fri 30 Nov 2018,
Return Sat 15 Dec 2018
from$ 327*Viewed: 39 minutes ago

Chicago (ORD) to Winnipeg (YWG)

Depart Tue 18 Dec 2018,
Return Wed 2 Jan 2019
from$ 664*Viewed: 39 minutes ago
*Prices have been available for round trips within the last 48 hours and may not be currently available. 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.
Deer with branched antlers stands near a lake in Canada

Plan ahead for flights from Chicago to Canada

from
to
Type
Dates
Price*
Chicago (ORD)
to Toronto (YYZ)
Roundtrip
Depart Tue 4 Dec 2018
Return Wed 19 Dec 2018
from$ 237*Viewed: 39 minutes ago
Chicago (ORD)
to Victoria (YYJ)
Roundtrip
Depart Tue 15 Jan 2019
Return Wed 30 Jan 2019
from$ 306*Viewed: 39 minutes ago
Chicago (ORD)
to Edmonton (YEG)
Roundtrip
Depart Tue 15 Jan 2019
Return Wed 30 Jan 2019
from$ 308*Viewed: 39 minutes ago
Chicago (ORD)
to Montreal (YUL)
Roundtrip
Depart Tue 4 Dec 2018
Return Wed 19 Dec 2018
from$ 327*Viewed: 39 minutes ago
Chicago (ORD)
to Vancouver (YVR)
Roundtrip
Depart Tue 4 Dec 2018
Return Wed 19 Dec 2018
from$ 356*Viewed: 39 minutes ago
Chicago (ORD)
to Halifax (YHZ)
Roundtrip
Depart Tue 15 Jan 2019
Return Wed 30 Jan 2019
from$ 362*Viewed: 39 minutes ago
Chicago (ORD)
to Québec (YQB)
Roundtrip
Depart Tue 15 Jan 2019
Return Wed 30 Jan 2019
from$ 522*Viewed: 39 minutes ago
Chicago (ORD)
to Calgary (YYC)
Roundtrip
Depart Sat 1 Dec 2018
Return Sun 16 Dec 2018
from$ 627*Viewed: 39 minutes ago
Chicago (ORD)
to Ottawa (YOW)
Roundtrip
Depart Tue 1 Jan 2019
Return Wed 16 Jan 2019
from$ 630*Viewed: 39 minutes ago
Chicago (ORD)
to Winnipeg (YWG)
Roundtrip
Depart Tue 18 Dec 2018
Return Wed 2 Jan 2019
from$ 664*Viewed: 39 minutes ago
*Prices have been available for round trips within the last 48 hours and may not be currently available. 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.