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 July , August 2026

27 Jul - 03 Aug $ 336.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
1 STOPS
YYC
Calgary
Pick dates
28 Jul - 08 Aug $ 661.00
YYC
Calgary
WestJet
DIRECT
CHI
Chicago
CHI
Chicago
WestJet
DIRECT
YYC
Calgary
Pick dates
31 Jul - 08 Aug $ 669.00
YYC
Calgary
WestJet
DIRECT
CHI
Chicago
CHI
Chicago
WestJet
DIRECT
YYC
Calgary
Pick dates

Last minute flights from Calgary to Chicago

28 Jul - 31 Jul $ 424.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YYC
Calgary
Pick dates
28 Jul - 31 Jul $ 424.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YYC
Calgary
Pick dates
30 Jul - 31 Jul $ 584.00
YYC
Calgary
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
YYC
Calgary
Pick dates

One-way flights to Chicago from Calgary

7:15 PM - 6:00 AM
United Airlines
1 Stops
13h 27m
YYC - CHI
$ 198
Kiwi
Pick dates
1:27 PM - 4:59 PM
United Airlines
1 Stops
6h 13m
YYC - CHI
$ 198
Kiwi
Pick dates
12:28 PM - 12:28 PM
United Airlines
0 Stops
3h 36m
YYC - CHI
$ 292
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.