Cheapest return flights from Toronto to Chicago in December from $148

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

Return flights

05 Dec - 07 Dec Porter Airlines (Canada) Ltd direct
12 Dec - 20 Dec Porter Airlines (Canada) Ltd direct
12 Dec - 01 Jan Porter Airlines (Canada) Ltd direct
05 Dec - 20 Dec Porter Airlines (Canada) Ltd direct
26 Dec - 01 Jan Porter Airlines (Canada) Ltd direct
25 Dec - 01 Jan Porter Airlines (Canada) Ltd direct

Also check the deals for one-way 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.

Book a cheap hotel in Chicago

Cheap car rent in Chicago

Feel free to contact us with any feedback or request another flight research.