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

One-Way flights

05 Dec	Porter Airlines (Canada) Ltd
02 Dec	Porter Airlines (Canada) Ltd
04 Dec	Porter Airlines (Canada) Ltd
06 Dec	Porter Airlines (Canada) Ltd
08 Dec	Porter Airlines (Canada) Ltd
10 Dec	Porter Airlines (Canada) Ltd
12 Dec	Porter Airlines (Canada) Ltd
03 Dec	Porter Airlines (Canada) Ltd
07 Dec	Porter Airlines (Canada) Ltd
09 Dec	Porter Airlines (Canada) Ltd

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

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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Cheapest one-way flights from Montreal to Chicago in December from 95€

One-Way flights