Book United Calgary to Chicago flight deals from $298

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Search flights from Calgary to Chicago (YYC - ORD)

October

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Tuesday 16th

Return Sunday 21st
from$ 298*Viewed: 19 hours ago

Friday 26th

Return Monday 29th
from$ 317*Viewed: 17 hours ago

Sunday 28th

Return Friday 2nd
from$ 316*Viewed: 1 day ago

November

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Thursday 1st

Return Sunday 4th
from$ 382*Viewed: 1 day ago

Friday 16th

Return Monday 19th
from$ 360*Viewed: 10 hours ago

December

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Friday 7th

Return Tuesday 11th
from$ 298*Viewed: 1 day ago

Thursday 13th

Return Friday 21st
from$ 393*Viewed: 1 day 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..
Cruise ships and tour boats docked by a ferris wheel and urban buildings at Navy Pier in Chicago

Plan ahead for flights from Calgary to Chicago

from
to
Type
Dates
Price*
Calgary (YYC)
to Chicago (ORD)
Roundtrip
Depart Tue 16 Oct 2018
Return Sun 21 Oct 2018
from$ 298*Viewed: 19 hours ago
Calgary (YYC)
to Chicago (ORD)
Roundtrip
Depart Fri 7 Dec 2018
Return Tue 11 Dec 2018
from$ 298*Viewed: 1 day ago
Calgary (YYC)
to Chicago (ORD)
Roundtrip
Depart Sun 28 Oct 2018
Return Fri 2 Nov 2018
from$ 316*Viewed: 1 day ago
Calgary (YYC)
to Chicago (ORD)
Roundtrip
Depart Fri 26 Oct 2018
Return Mon 29 Oct 2018
from$ 317*Viewed: 17 hours ago
Calgary (YYC)
to Chicago (ORD)
Roundtrip
Depart Fri 16 Nov 2018
Return Mon 19 Nov 2018
from$ 360*Viewed: 10 hours ago
Calgary (YYC)
to Chicago (ORD)
Roundtrip
Depart Thu 1 Nov 2018
Return Sun 4 Nov 2018
from$ 382*Viewed: 1 day ago
Calgary (YYC)
to Chicago (ORD)
Roundtrip
Depart Thu 13 Dec 2018
Return Fri 21 Dec 2018
from$ 393*Viewed: 1 day ago
Calgary (YYC)
to Chicago (ORD)
Roundtrip
Depart Thu 18 Oct 2018
Return Mon 22 Oct 2018
from$ 461*Viewed: 20 hours ago
Calgary (YYC)
to Chicago (ORD)
Roundtrip
Depart Fri 19 Oct 2018
Return Mon 22 Oct 2018
from$ 461*Viewed: 19 hours ago
Calgary (YYC)
to Chicago (ORD)
Roundtrip
Depart Fri 5 Oct 2018
Return Mon 8 Oct 2018
from$ 546*Viewed: 13 hours 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.