AirHint found the following cheapest return flights from Calgary (YYC) to Chicago (ORD) in May 2026 (see full year).
Return flights
| 27 May - 29 May | WestJet | direct | |
| 20 May - 27 May | WestJet | direct | |
| 07 May - 11 May | WestJet | direct | |
| 09 May - 11 May | WestJet | ||
| 15 May - 18 May | Delta | ||
| 15 May - 18 May | WestJet | direct |
Also check the deals for one-way flights from Calgary to Chicago in May.
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