Cheapest return flights from Montreal to Chicago in December from $242

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

Return flights

27 Dec - 13 Jan Porter Airlines (Canada) Ltd
05 Dec - 12 Dec Porter Airlines (Canada) Ltd
05 Dec - 07 Dec Porter Airlines (Canada) Ltd
24 Dec - 13 Jan Porter Airlines (Canada) Ltd
24 Dec - 12 Jan Porter Airlines (Canada) Ltd
04 Dec - 08 Dec Porter Airlines (Canada) Ltd
07 Dec - 14 Dec Porter Airlines (Canada) Ltd
08 Dec - 15 Dec Porter Airlines (Canada) Ltd
04 Dec - 07 Dec Porter Airlines (Canada) Ltd
05 Dec - 08 Dec Porter Airlines (Canada) Ltd
11 Dec - 15 Dec Porter Airlines (Canada) Ltd
10 Dec - 15 Dec Porter Airlines (Canada) Ltd
24 Dec - 25 Jan Delta
25 Dec - 13 Jan Porter Airlines (Canada) Ltd
29 Dec - 13 Jan Porter Airlines (Canada) Ltd
30 Dec - 13 Jan Porter Airlines (Canada) Ltd
25 Dec - 12 Jan Porter Airlines (Canada) Ltd
29 Dec - 19 Jan Porter Airlines (Canada) Ltd
30 Dec - 19 Jan Porter Airlines (Canada) Ltd
01 Dec - 03 Dec Porter Airlines (Canada) Ltd

Also check the deals for one-way flights from Montreal 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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