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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 September , October 2026

29 Sep - 03 Oct $ 345.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
1 STOPS
YYC
Calgary
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30 Sep - 10 Oct $ 409.00
YYC
Calgary
Air Canada
2 STOPS
CHI
Chicago
CHI
Chicago
Air Canada
2 STOPS
YYC
Calgary
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29 Sep - 02 Oct $ 762.00
YYC
Calgary
WestJet
DIRECT
CHI
Chicago
CHI
Chicago
WestJet
DIRECT
YYC
Calgary
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Last minute flights from Calgary to Chicago

29 Sep - 30 Sep $ 383.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
1 STOPS
YYC
Calgary
Pick dates
29 Sep - 30 Sep $ 383.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
1 STOPS
YYC
Calgary
Pick dates
29 Sep - 30 Sep $ 723.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YYC
Calgary
Pick dates

One-way flights to Chicago from Calgary

8:30 PM - 8:05 AM
Air Canada
2 Stops
11h 30m
YYC - CHI
$ 234
Kiwi
Pick dates
12:30 PM - 12:30 PM
United Airlines
0 Stops
3h 35m
YYC - CHI
$ 241
Kiwi
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7:00 AM - 7:00 AM
Porter Airlines
0 Stops
3h 29m
YYC - CHI
$ 289
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.