Cheapest one-way flights from Toronto to Chicago in December from $111

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

One-Way flights

09 Dec Porter Airlines (Canada) Ltd direct
07 Dec Porter Airlines (Canada) Ltd direct
05 Dec Porter Airlines (Canada) Ltd direct
08 Dec Porter Airlines (Canada) Ltd direct
10 Dec Porter Airlines (Canada) Ltd direct
11 Dec Porter Airlines (Canada) Ltd direct
25 Dec Porter Airlines (Canada) Ltd direct
19 Dec Porter Airlines (Canada) Ltd direct
18 Dec Porter Airlines (Canada) Ltd direct
30 Dec Porter Airlines (Canada) Ltd direct

Also check the deals for return flights from Toronto to Chicago in December.

Skyscanner

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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