Cheap flights from Chicago to Calgary South

View AU$138 flight on Tue, 16 Sep. 2025Opens in a new window

Popular airlines from Chicago to Calgary South

  • Delta

    Delta

  • WestJet

    WestJet

  • American Airlines

    American Airlines

  • Air Canada

    Air Canada

  • Alaska Airlines

    Alaska Airlines

  • United

    United

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Cheap Flights from Chicago (CHI) to Calgary South (YYC)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Tue, 16 Sep. - Tue, 23 Sep.
ORD
Chicago
YYC
Calgary
AU$338 Return, found 16 hours ago
AU$338
Return
found 16 hours ago
Select Air Canada flight, departing Tue, 16 Sep. from Chicago to Calgary, returning Tue, 23 Sep., priced at AU$338 found 16 hours ago
United
Tue, 16 Sep. - Tue, 23 Sep.
ORD
Chicago
YYC
Calgary
AU$341 Return, found 16 hours ago
AU$341
Return
found 16 hours ago
Select United flight, departing Tue, 16 Sep. from Chicago to Calgary, returning Tue, 23 Sep., priced at AU$341 found 16 hours ago
United
Fri, 31 Oct. - Sun, 2 Nov.
ORD
Chicago
YYC
Calgary
AU$345 Return, found 1 day ago
AU$345
Return
found 1 day ago
Select United flight, departing Fri, 31 Oct. from Chicago to Calgary, returning Sun, 2 Nov., priced at AU$345 found 1 day ago
Delta
Tue, 16 Sep. - Tue, 23 Sep.
ORD
Chicago
YYC
Calgary
AU$347 Return, found 16 hours ago
AU$347
Return
found 16 hours ago
Select Delta flight, departing Tue, 16 Sep. from Chicago to Calgary, returning Tue, 23 Sep., priced at AU$347 found 16 hours ago
WestJet
Fri, 31 Oct. - Sun, 2 Nov.
ORD
Chicago
YYC
Calgary
AU$367 Return, found 1 day ago
AU$367
Return
found 1 day ago
Select WestJet flight, departing Fri, 31 Oct. from Chicago to Calgary, returning Sun, 2 Nov., priced at AU$367 found 1 day ago
American Airlines
Tue, 16 Sep. - Tue, 23 Sep.
ORD
Chicago
YYC
Calgary
AU$442 Return, found 16 hours ago
AU$442
Return
found 16 hours ago
Select American Airlines flight, departing Tue, 16 Sep. from Chicago to Calgary, returning Tue, 23 Sep., priced at AU$442 found 16 hours ago

Find the cheapest month to fly from Chicago (CHI) to Calgary (YYC)

April is typically the cheapest month to fly

From AU$248 - AU$815 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.