Cheapest return flights from Calgary to Chicago in September from $245

AirHint found the following cheapest return flights from Calgary (YYC) to Chicago (ORD) in September 2026 (see full year).

Return flights

23 Sep - 27 Sep Delta
23 Sep - 27 Sep Air Canada direct

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

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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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