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

One-Way flights

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

Also check the deals for return flights from Chicago to Montreal 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 Chicago to Montreal in December from 52€

One-Way flights