AirHint found the following cheapest return flights from Calgary (YYC) to Chicago (ORD) in February 2026 (see full year).

Return flights

27 Feb - 06 Mar	WestJet	direct
20 Feb - 27 Feb	WestJet	direct
06 Feb - 06 Mar	WestJet	direct
20 Feb - 23 Feb	WestJet	direct
06 Feb - 08 Feb	Delta
19 Feb - 24 Feb	Delta
18 Feb - 23 Feb	Porter Airlines (Canada) Ltd
15 Feb - 18 Feb	Delta
02 Feb - 07 Feb	Delta
02 Feb - 06 Feb	WestJet	direct
10 Feb - 15 Feb	Delta
13 Feb - 16 Feb	WestJet	direct

Also check the deals for one-way flights from Calgary to Chicago in February.

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

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Cheapest return flights from Calgary to Chicago in February from $197

Return flights