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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 March , April 2026

30 Mar - 24 Apr $ 382.00
YYC
Calgary
WestJet
DIRECT
CHI
Chicago
CHI
Chicago
WestJet
DIRECT
YYC
Calgary
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16 Mar - 10 Apr $ 492.00
YYC
Calgary
WestJet
DIRECT
CHI
Chicago
CHI
Chicago
WestJet
DIRECT
YYC
Calgary
Pick dates
16 Mar - 06 Apr $ 512.00
YYC
Calgary
WestJet
DIRECT
CHI
Chicago
CHI
Chicago
WestJet
DIRECT
YYC
Calgary
Pick dates

Last minute flights from Calgary to Chicago

17 Mar - 31 Mar $ 638.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YYC
Calgary
Pick dates
16 Mar - 31 Mar $ 641.00
YYC
Calgary
Alaska Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Alaska Airlines
1 STOPS
YYC
Calgary
Pick dates
16 Mar - 31 Mar $ 1,077.00
YYC
Calgary
WestJet
DIRECT
CHI
Chicago
CHI
Chicago
WestJet
1 STOPS
YYC
Calgary
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One-way flights to Chicago from Calgary

12:32 PM - 12:32 PM
United Airlines
0 Stops
3h 33m
YYC - CHI
$ 148
Kiwi
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12:32 PM - 12:32 PM
United Airlines
0 Stops
3h 33m
YYC - CHI
$ 148
Kiwi
Pick dates
12:32 PM - 12:32 PM
United Airlines
0 Stops
3h 32m
YYC - CHI
$ 519
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.