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

Return flights

29 Aug - 03 Sep	WestJet	direct
26 Aug - 29 Aug	WestJet	direct
21 Aug - 27 Aug	WestJet	direct
29 Aug - 02 Sep	WestJet	direct
31 Aug - 02 Sep	WestJet	direct
21 Aug - 24 Aug	WestJet	direct
30 Aug - 03 Sep	Delta
12 Aug - 20 Aug	Delta
29 Aug - 04 Sep	WestJet	direct
18 Aug - 25 Aug	Delta
30 Aug - 02 Sep	Delta
29 Aug - 01 Sep	Delta
08 Aug - 11 Aug	WestJet
19 Aug - 23 Aug	WestJet
05 Aug - 14 Aug	WestJet
10 Aug - 17 Aug	WestJet
05 Aug - 21 Aug	WestJet
28 Aug - 01 Sep	Delta
28 Aug - 01 Sep	United	direct
29 Aug - 01 Sep	United	direct

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

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 Calgary to Chicago in August from 138€

Return flights