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

Return flights

18 Sep - 23 Sep	WestJet	direct
25 Sep - 05 Oct	WestJet
26 Sep - 30 Sep	WestJet	direct
26 Sep - 05 Oct	WestJet
26 Sep - 04 Oct	WestJet
30 Sep - 08 Oct	United
16 Sep - 20 Sep	WestJet
03 Sep - 12 Sep	WestJet
25 Sep - 28 Sep	WestJet
05 Sep - 07 Sep	WestJet
03 Sep - 07 Sep	WestJet
22 Sep - 26 Sep	WestJet
09 Sep - 15 Sep	WestJet
05 Sep - 13 Sep	WestJet
25 Sep - 02 Oct	WestJet
26 Sep - 04 Oct	American Airlines	direct
26 Sep - 05 Oct	American Airlines	direct
25 Sep - 05 Oct	American Airlines	direct
25 Sep - 02 Oct	WestJet	direct
30 Sep - 08 Oct	Air Canada	direct

Also check the deals for one-way flights from Chicago to Calgary 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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Cheapest return flights from Chicago to Calgary in September from 118€

Return flights