Cheap flights from Calgary to Central United States

View AU$190 flight on Tue, 28 Oct. 2025Opens in a new window

Popular airlines from Calgary to Central United States

  • American Airlines

    American Airlines

  • Air Canada

    Air Canada

  • Alaska Airlines

    Alaska Airlines

  • Delta

    Delta

  • United

    United

  • WestJet

    WestJet

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Cheap Flights from Calgary (YYC) to Central United States (CHI)

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
Thu, 16 Oct. - Thu, 23 Oct.
YYC
Calgary
ORD
Chicago
AU$328 Return, found 4 days ago
AU$328
Return
found 4 days ago
Select Air Canada flight, departing Thu, 16 Oct. from Calgary to Chicago, returning Thu, 23 Oct., priced at AU$328 found 4 days ago
United
Wed, 8 Oct. - Wed, 22 Oct.
YYC
Calgary
ORD
Chicago
AU$337 Return, found 4 days ago
AU$337
Return
found 4 days ago
Select United flight, departing Wed, 8 Oct. from Calgary to Chicago, returning Wed, 22 Oct., priced at AU$337 found 4 days ago
Air Canada
Wed, 1 Oct. - Wed, 8 Oct.
YYC
Calgary
ORD
Chicago
AU$338 Return, found 3 days ago
AU$338
Return
found 3 days ago
Select Air Canada flight, departing Wed, 1 Oct. from Calgary to Chicago, returning Wed, 8 Oct., priced at AU$338 found 3 days ago
WestJet
Thu, 16 Oct. - Thu, 23 Oct.
YYC
Calgary
ORD
Chicago
AU$338 Return, found 4 days ago
AU$338
Return
found 4 days ago
Select WestJet flight, departing Thu, 16 Oct. from Calgary to Chicago, returning Thu, 23 Oct., priced at AU$338 found 4 days ago
Delta
Wed, 1 Oct. - Wed, 8 Oct.
YYC
Calgary
ORD
Chicago
AU$346 Return, found 3 days ago
AU$346
Return
found 3 days ago
Select Delta flight, departing Wed, 1 Oct. from Calgary to Chicago, returning Wed, 8 Oct., priced at AU$346 found 3 days ago
American Airlines
Thu, 2 Oct. - Sat, 11 Oct.
YYC
Calgary
IAH
Houston
AU$397 Return, found 6 days ago
AU$397
Return
found 6 days ago
Select American Airlines flight, departing Thu, 2 Oct. from Calgary to Houston, returning Sat, 11 Oct., priced at AU$397 found 6 days ago

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

September is typically the cheapest month to fly

From AU$224 - AU$434 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.