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Cheap flights from Calgary (YYC) to Chicago (CHI)

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0 Children (2~11)
0 Infants (0~2)
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How to find the cheapest flight from Calgary (YYC) to Chicago (CHI)

How to find the cheapest flight from Calgary (YYC) to Chicago (CHI)
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How to find the cheapest flight from Calgary (YYC) to Chicago (CHI)
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How to find the cheapest flight from Calgary (YYC) to Chicago (CHI)
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Cheap flights from Calgary to Chicago in November , December 2026

17 Nov - 05 Dec $ 345.00
YYC
Calgary
Air Canada
1 STOPS
CHI
Chicago
CHI
Chicago
Air Canada
2 STOPS
YYC
Calgary
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26 Nov - 02 Dec $ 355.00
YYC
Calgary
Air Canada
1 STOPS
CHI
Chicago
CHI
Chicago
Air Canada
1 STOPS
YYC
Calgary
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19 Nov - 05 Dec $ 829.00
YYC
Calgary
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YYC
Calgary
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Last minute flights from Calgary to Chicago

26 Nov - 30 Nov $ 315.00
YYC
Calgary
Air Canada
1 STOPS
CHI
Chicago
CHI
Chicago
Air Canada
1 STOPS
YYC
Calgary
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20 Nov - 30 Nov $ 330.00
YYC
Calgary
Air Canada
1 STOPS
CHI
Chicago
CHI
Chicago
Air Canada
1 STOPS
YYC
Calgary
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19 Nov - 30 Nov $ 1,624.00
YYC
Calgary
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YYC
Calgary
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One-way flights to Chicago from Calgary

1:20 AM - 8:20 AM
Air Canada
1 Stops
8h 3m
YYC - CHI
$ 187
Kiwi
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9:09 AM - 11:23 AM
Alaska Airlines
1 Stops
8h 28m
YYC - CHI
$ 190
Kiwi
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9:09 AM - 11:23 AM
Alaska Airlines
1 Stops
8h 28m
YYC - CHI
$ 193
Kiwi
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How to find the cheapest flight from Calgary (YYC) to Chicago (CHI)

Related info for your journey
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How to find the cheapest flight from Calgary (YYC) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Calgary (YYC) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.