Cheapest return flights from Toronto to Chicago in December from $180

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

Return flights

19 Dec - 05 Jan Porter Airlines (Canada) Ltd direct
20 Dec - 05 Jan Porter Airlines (Canada) Ltd direct
22 Dec - 05 Jan Porter Airlines (Canada) Ltd direct
12 Dec - 15 Dec Porter Airlines (Canada) Ltd direct
01 Dec - 03 Dec Porter Airlines (Canada) Ltd direct
11 Dec - 15 Dec Porter Airlines (Canada) Ltd direct
07 Dec - 09 Dec Porter Airlines (Canada) Ltd direct
02 Dec - 23 Dec Porter Airlines (Canada) Ltd direct
07 Dec - 19 Dec Porter Airlines (Canada) Ltd direct
01 Dec - 14 Dec Porter Airlines (Canada) Ltd direct
04 Dec - 08 Dec Porter Airlines (Canada) Ltd direct
24 Dec - 06 Jan Porter Airlines (Canada) Ltd direct
31 Dec - 06 Jan Porter Airlines (Canada) Ltd direct
17 Dec - 06 Jan Porter Airlines (Canada) Ltd direct
18 Dec - 06 Jan Porter Airlines (Canada) Ltd direct
25 Dec - 06 Jan Porter Airlines (Canada) Ltd direct
05 Dec - 08 Dec Porter Airlines (Canada) Ltd direct
05 Dec - 06 Dec Porter Airlines (Canada) Ltd direct
24 Dec - 05 Jan Porter Airlines (Canada) Ltd direct
31 Dec - 05 Jan Porter Airlines (Canada) Ltd direct

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

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