Cheapest return flights from Chicago to Toronto in December from $314

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

Return flights

30 Dec - 20 Jan Porter Airlines (Canada) Ltd direct
31 Dec - 20 Jan Porter Airlines (Canada) Ltd direct
25 Dec - 06 Jan Porter Airlines (Canada) Ltd direct
18 Dec - 18 Jan Porter Airlines (Canada) Ltd direct
25 Dec - 07 Jan Porter Airlines (Canada) Ltd direct
30 Dec - 05 Jan Porter Airlines (Canada) Ltd direct
25 Dec - 14 Jan Porter Airlines (Canada) Ltd direct
24 Dec - 05 Jan Porter Airlines (Canada) Ltd direct
25 Dec - 05 Jan Porter Airlines (Canada) Ltd direct
31 Dec - 04 Jan Porter Airlines (Canada) Ltd direct
26 Dec - 31 Dec Porter Airlines (Canada) Ltd direct
25 Dec - 31 Dec Porter Airlines (Canada) Ltd direct
30 Dec - 31 Dec Porter Airlines (Canada) Ltd direct
15 Dec - 19 Dec Porter Airlines (Canada) Ltd direct
21 Dec - 31 Dec Porter Airlines (Canada) Ltd direct
25 Dec - 26 Dec Porter Airlines (Canada) Ltd direct
25 Dec - 27 Dec Porter Airlines (Canada) Ltd direct
24 Dec - 27 Dec Porter Airlines (Canada) Ltd direct
25 Dec - 29 Dec Porter Airlines (Canada) Ltd direct
18 Dec - 22 Dec Porter Airlines (Canada) Ltd direct

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

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