Cheapest one-way flights from Toronto to Chicago in December from $107

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

One-Way flights

01 Dec Porter Airlines (Canada) Ltd direct
05 Dec Porter Airlines (Canada) Ltd direct
17 Dec Porter Airlines (Canada) Ltd direct
04 Dec Porter Airlines (Canada) Ltd direct
13 Dec Porter Airlines (Canada) Ltd direct
16 Dec Porter Airlines (Canada) Ltd direct
21 Dec Porter Airlines (Canada) Ltd direct
26 Dec Porter Airlines (Canada) Ltd direct
30 Dec Porter Airlines (Canada) Ltd direct
25 Dec Porter Airlines (Canada) Ltd direct

Also check the deals for return 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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