AirHint found the following cheapest return flights from Toronto (YYZ) to Chicago (ORD) in December 2025 (see full year).

Return flights

24 Dec - 31 Dec	Air Canada	direct
10 Dec - 17 Dec	Air Canada
23 Dec - 27 Dec	Air Canada
23 Dec - 28 Dec	Air Canada
21 Dec - 22 Jan	Air Canada	direct
10 Dec - 17 Dec	Air Canada	direct
23 Dec - 27 Dec	Air Canada	direct
18 Dec - 25 Dec	Air Canada	direct
23 Dec - 31 Dec	Air Canada	direct
15 Dec - 02 Jan	United	direct
27 Dec - 03 Jan	Air Canada	direct
31 Dec - 04 Jan	Air Canada	direct
29 Dec - 01 Jan	Air Canada	direct

Also check the deals for one-way flights from Toronto to Chicago in December.

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 Toronto to Chicago in December from 121€

Return flights