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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 July , August 2026

29 Jul - 05 Aug $ 336.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
1 STOPS
YYC
Calgary
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28 Jul - 08 Aug $ 713.00
YYC
Calgary
WestJet
DIRECT
CHI
Chicago
CHI
Chicago
WestJet
DIRECT
YYC
Calgary
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28 Jul - 04 Aug $ 714.00
YYC
Calgary
Air Canada
2 STOPS
CHI
Chicago
CHI
Chicago
Air Canada
1 STOPS
YYC
Calgary
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Last minute flights from Calgary to Chicago

28 Jul - 31 Jul $ 440.00
YYC
Calgary
United Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YYC
Calgary
Pick dates
28 Jul - 31 Jul $ 440.00
YYC
Calgary
United Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YYC
Calgary
Pick dates
28 Jul - 31 Jul $ 585.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YYC
Calgary
Pick dates

One-way flights to Chicago from Calgary

6:00 AM - 6:00 PM
United Airlines
1 Stops
14h 39m
YYC - CHI
$ 198
Kiwi
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12:30 PM - 3:31 PM
Air Canada
1 Stops
6h 35m
YYC - CHI
$ 232
Kiwi
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12:28 PM - 12:28 PM
United Airlines
0 Stops
3h 36m
YYC - CHI
$ 317
Kiwi
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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.