Cheap flights from Calgary to Northwest Chicago

View AU$175 flight on Tue, 9 Sep. 2025Opens in a new window

Popular airlines from Calgary to Northwest Chicago

  • 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 Calgary (YYC) to Northwest Chicago (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.

WestJet
Tue, 9 Sep. - Tue, 16 Sep.
YYC
Calgary
ORD
Chicago
AU$286 Return, found 21 hours ago
AU$286
Return
found 21 hours ago
Select WestJet flight, departing Tue, 9 Sep. from Calgary to Chicago, returning Tue, 16 Sep., priced at AU$286 found 21 hours ago
Air Canada
Tue, 9 Sep. - Tue, 16 Sep.
YYC
Calgary
ORD
Chicago
AU$301 Return, found 21 hours ago
AU$301
Return
found 21 hours ago
Select Air Canada flight, departing Tue, 9 Sep. from Calgary to Chicago, returning Tue, 16 Sep., priced at AU$301 found 21 hours ago
Air Canada
Tue, 9 Sep. - Tue, 16 Sep.
YYC
Calgary
ORD
Chicago
AU$305 Return, found 21 hours ago
AU$305
Return
found 21 hours ago
Select Air Canada flight, departing Tue, 9 Sep. from Calgary to Chicago, returning Tue, 16 Sep., priced at AU$305 found 21 hours ago
United
Wed, 8 Oct. - Wed, 22 Oct.
YYC
Calgary
ORD
Chicago
AU$337 Return, found 6 days ago
AU$337
Return
found 6 days ago
Select United flight, departing Wed, 8 Oct. from Calgary to Chicago, returning Wed, 22 Oct., priced at AU$337 found 6 days ago
Delta
Tue, 9 Sep. - Tue, 16 Sep.
YYC
Calgary
MDW
Chicago
AU$342 Return, found 21 hours ago
AU$342
Return
found 21 hours ago
Select Delta flight, departing Tue, 9 Sep. from Calgary to Chicago, returning Tue, 16 Sep., priced at AU$342 found 21 hours ago
American Airlines
Thu, 28 Aug. - Wed, 3 Sep.
YYC
Calgary
ORD
Chicago
AU$429 Return, found 22 hours ago
AU$429
Return
found 22 hours ago
Select American Airlines flight, departing Thu, 28 Aug. from Calgary to Chicago, returning Wed, 3 Sep., priced at AU$429 found 22 hours 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.