Cheapest one-way flights from Calgary to Chicago in October from 81€

AirHint found the following cheapest one-way flights from Calgary (YYC) to Chicago (ORD) in October 2025 (see full year).

One-Way flights

04 Oct WestJet direct
06 Oct WestJet direct
13 Oct Air Canada
07 Oct Air Canada
08 Oct Air Canada
21 Oct Air Canada
13 Oct WestJet direct
07 Oct United direct
21 Oct United direct
08 Oct United direct

Also check the deals for return flights from Calgary to Chicago in October.

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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