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

Return flights

04 Oct - 12 Oct	WestJet	direct
13 Oct - 17 Oct	Air Canada
13 Oct - 17 Oct	WestJet	direct
04 Oct - 13 Oct	WestJet
31 Oct - 03 Nov	Delta
30 Oct - 03 Nov	United	direct
03 Oct - 13 Oct	WestJet
31 Oct - 03 Nov	United	direct
11 Oct - 13 Oct	Delta
11 Oct - 13 Oct	WestJet	direct
04 Oct - 13 Oct	WestJet	direct
03 Oct - 13 Oct	WestJet	direct

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

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.

Book a cheap hotel in Chicago

Cheap car rent in Chicago

Cheapest return flights from Calgary to Chicago in October from 122€

Return flights