AirHint found the following cheapest one-way flights from Calgary (YYC) to Chicago (ORD) in May 2026 (see full year).
One-Way flights
| 27 May | WestJet | direct | |
| 02 May | Air Canada | ||
| 18 May | WestJet | direct | |
| 13 May | Air Canada | ||
| 02 May | American Airlines | direct | |
| 13 May | United | direct |
Also check the deals for return flights from Calgary to Chicago in May.
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