AirHint found the following cheapest one-way flights from Calgary (YYC) to Chicago (ORD) in September 2025 (see full year).
One-Way flights
| 24 Sep | WestJet | direct | |
| 20 Sep | Air Canada | ||
| 21 Sep | Air Canada | ||
| 04 Sep | Air Canada | ||
| 04 Sep | WestJet | direct | |
| 21 Sep | WestJet | direct |
Also check the deals for return flights from Calgary to Chicago in September.
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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