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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

30 Apr - 07 May $ 264.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YYC
Calgary
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30 Apr - 10 May $ 458.00
YYC
Calgary
WestJet
DIRECT
CHI
Chicago
CHI
Chicago
WestJet
DIRECT
YYC
Calgary
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24 Apr - 10 May $ 678.00
YYC
Calgary
WestJet
DIRECT
CHI
Chicago
CHI
Chicago
WestJet
DIRECT
YYC
Calgary
Pick dates

Last minute flights from Calgary to Chicago

25 Apr - 30 Apr $ 502.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YYC
Calgary
Pick dates
25 Apr - 01 May $ 512.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
1 STOPS
YYC
Calgary
Pick dates
29 Apr - 30 Apr $ 589.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
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
$ 171
Kiwi
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1:27 PM - 5:40 PM
United Airlines
1 Stops
6h 50m
YYC - CHI
$ 186
Kiwi
Pick dates
12:34 PM - 12:34 PM
United Airlines
0 Stops
3h 27m
YYC - CHI
$ 223
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.