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

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1 Adults (11+)
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 2025

24 Nov - 15 Dec $ 188.00
YYC
Calgary
WestJet
DIRECT
CHI
Chicago
CHI
Chicago
WestJet
DIRECT
YYC
Calgary
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24 Nov - 08 Dec $ 204.00
YYC
Calgary
WestJet
DIRECT
CHI
Chicago
CHI
Chicago
WestJet
DIRECT
YYC
Calgary
Pick dates
24 Nov - 05 Dec $ 333.00
YYC
Calgary
WestJet
DIRECT
CHI
Chicago
CHI
Chicago
WestJet
DIRECT
YYC
Calgary
Pick dates

Last minute flights from Calgary to Chicago

25 Nov - 30 Nov $ 240.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YYC
Calgary
Pick dates
23 Nov - 30 Nov $ 240.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YYC
Calgary
Pick dates
28 Nov - 30 Nov $ 488.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YYC
Calgary
Pick dates

One-way flights to Chicago from Calgary

9:00 AM - 9:00 AM
WestJet
0 Stops
3h 35m
YYC - CHI
$ 115
Kiwi
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12:37 PM - 12:37 PM
United Airlines
0 Stops
3h 33m
YYC - CHI
$ 145
Kiwi
Pick dates
12:37 PM - 12:37 PM
United Airlines
0 Stops
3h 33m
YYC - CHI
$ 251
Kiwi
Pick dates

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.