Earn point on your loyalty program!arrow arc left

Cheap flights from Calgary (YYC) to Chicago (CHI)

Know your dates, get live prices in seconds
airplane logo

pin logo

calendar
Departure
calendar backward
Return
airplane logo
1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
Save up to 31%
Book Flight + Hotel at the same time

How to find the cheapest flight from Calgary (YYC) to Chicago (CHI)

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.
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.

Cheap flights from Calgary to Chicago in December 2025 , January 2026

31 Dec - 07 Jan $ 274.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
1 STOPS
YYC
Calgary
Pick dates
22 Dec - 09 Jan $ 338.00
YYC
Calgary
WestJet
DIRECT
CHI
Chicago
CHI
Chicago
WestJet
DIRECT
YYC
Calgary
Pick dates
19 Dec - 09 Jan $ 440.00
YYC
Calgary
WestJet
DIRECT
CHI
Chicago
CHI
Chicago
WestJet
DIRECT
YYC
Calgary
Pick dates

Last minute flights from Calgary to Chicago

24 Dec - 31 Dec $ 302.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
1 STOPS
YYC
Calgary
Pick dates
24 Dec - 31 Dec $ 302.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
1 STOPS
YYC
Calgary
Pick dates
24 Dec - 31 Dec $ 741.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YYC
Calgary
Pick dates

One-way flights to Chicago from Calgary

2:13 PM - 5:35 PM
United Airlines
1 Stops
5h 55m
YYC - CHI
$ 129
Kiwi
Pick dates
6:15 AM - 5:35 PM
United Airlines
1 Stops
13h 53m
YYC - CHI
$ 129
Kiwi
Pick dates
12:37 PM - 12:37 PM
United Airlines
0 Stops
3h 31m
YYC - CHI
$ 299
Kiwi
Pick dates

How to find the cheapest flight from Calgary (YYC) to Chicago (CHI)

Related info for your journey
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.
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.