Cheapest return flights from Toronto to Chicago in December from $207

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

Return flights

03 Dec - 03 Dec Porter Airlines (Canada) Ltd direct
03 Dec - 10 Dec Porter Airlines (Canada) Ltd direct
08 Dec - 10 Dec Porter Airlines (Canada) Ltd direct
03 Dec - 07 Dec Porter Airlines (Canada) Ltd direct
07 Dec - 10 Dec Porter Airlines (Canada) Ltd direct
03 Dec - 05 Dec Porter Airlines (Canada) Ltd direct
01 Dec - 03 Dec Porter Airlines (Canada) Ltd direct
07 Dec - 07 Dec Porter Airlines (Canada) Ltd direct
01 Dec - 10 Dec Porter Airlines (Canada) Ltd direct
03 Dec - 15 Dec Porter Airlines (Canada) Ltd direct
25 Dec - 15 Jan Porter Airlines (Canada) Ltd direct
30 Dec - 15 Jan Porter Airlines (Canada) Ltd direct
21 Dec - 08 Jan Porter Airlines (Canada) Ltd direct
19 Dec - 08 Jan Porter Airlines (Canada) Ltd direct
20 Dec - 08 Jan Porter Airlines (Canada) Ltd direct
25 Dec - 08 Jan Porter Airlines (Canada) Ltd direct
24 Dec - 08 Jan Porter Airlines (Canada) Ltd direct
30 Dec - 08 Jan Porter Airlines (Canada) Ltd direct
24 Dec - 04 Jan Porter Airlines (Canada) Ltd direct
31 Dec - 15 Jan Porter Airlines (Canada) Ltd direct

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

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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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