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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 April , May 2026

27 Apr - 27 May $ 245.00
YYC
Calgary
WestJet
DIRECT
CHI
Chicago
CHI
Chicago
WestJet
DIRECT
YYC
Calgary
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12 Apr - 03 May $ 516.00
YYC
Calgary
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
DIRECT
YYC
Calgary
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06 Apr - 03 May $ 535.00
YYC
Calgary
WestJet
DIRECT
CHI
Chicago
CHI
Chicago
WestJet
DIRECT
YYC
Calgary
Pick dates

Last minute flights from Calgary to Chicago

27 Apr - 30 Apr $ 272.00
YYC
Calgary
WestJet
DIRECT
CHI
Chicago
CHI
Chicago
WestJet
DIRECT
YYC
Calgary
Pick dates
12 Apr - 30 Apr $ 516.00
YYC
Calgary
WestJet
1 STOPS
CHI
Chicago
CHI
Chicago
WestJet
DIRECT
YYC
Calgary
Pick dates
06 Apr - 30 Apr $ 535.00
YYC
Calgary
WestJet
DIRECT
CHI
Chicago
CHI
Chicago
WestJet
DIRECT
YYC
Calgary
Pick dates

One-way flights to Chicago from Calgary

12:34 PM - 12:34 PM
United Airlines
0 Stops
3h 27m
YYC - CHI
$ 152
Kiwi
Pick dates
1:27 PM - 5:44 PM
United Airlines
1 Stops
6h 53m
YYC - CHI
$ 167
Kiwi
Pick dates
12:34 PM - 12:34 PM
United Airlines
0 Stops
3h 27m
YYC - CHI
$ 211
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.