Cheapest return flights from Chicago to Calgary in September from $159

AirHint found the following cheapest return flights from Chicago (ORD) to Calgary (YYC) in September 2025 (see full year).

Return flights

07 Sep - 13 Sep WestJet direct
13 Sep - 18 Sep WestJet direct
10 Sep - 14 Sep WestJet direct
11 Sep - 16 Sep WestJet direct
13 Sep - 17 Sep WestJet direct
04 Sep - 17 Sep WestJet direct
05 Sep - 10 Sep WestJet direct
14 Sep - 17 Sep WestJet direct
10 Sep - 15 Sep WestJet direct

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

Skyscanner

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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