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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 October , November 2026

31 Oct - 07 Nov $ 364.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YYC
Calgary
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20 Oct - 07 Nov $ 427.00
YYC
Calgary
Air Canada
1 STOPS
CHI
Chicago
CHI
Chicago
Air Canada
1 STOPS
YYC
Calgary
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22 Oct - 07 Nov $ 1,096.00
YYC
Calgary
WestJet
DIRECT
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YYC
Calgary
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Last minute flights from Calgary to Chicago

26 Oct - 31 Oct $ 364.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YYC
Calgary
Pick dates
28 Oct - 31 Oct $ 368.00
YYC
Calgary
United Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YYC
Calgary
Pick dates
28 Oct - 31 Oct $ 648.00
YYC
Calgary
Air Canada
DIRECT
CHI
Chicago
CHI
Chicago
Air Canada
DIRECT
YYC
Calgary
Pick dates

One-way flights to Chicago from Calgary

12:37 PM - 12:37 PM
United Airlines
0 Stops
3h 33m
YYC - CHI
$ 198
Kiwi
Pick dates
12:30 PM - 12:30 PM
United Airlines
0 Stops
3h 35m
YYC - CHI
$ 199
Kiwi
Pick dates
12:37 PM - 12:37 PM
United Airlines
0 Stops
3h 33m
YYC - CHI
$ 414
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.