Cheapest return flights from Montreal to Chicago in January from $141

AirHint found the following cheapest return flights from Montreal (YUL) to Chicago (MDW) in January 2026 (see full year).

Return flights

12 Jan - 19 Jan Porter Airlines (Canada) Ltd
22 Jan - 26 Jan Porter Airlines (Canada) Ltd
23 Jan - 26 Jan Porter Airlines (Canada) Ltd
16 Jan - 23 Jan Porter Airlines (Canada) Ltd
09 Jan - 29 Jan Porter Airlines (Canada) Ltd
09 Jan - 27 Jan Porter Airlines (Canada) Ltd
26 Jan - 29 Jan Porter Airlines (Canada) Ltd
26 Jan - 30 Jan Porter Airlines (Canada) Ltd
26 Jan - 27 Jan Porter Airlines (Canada) Ltd
29 Jan - 30 Jan Porter Airlines (Canada) Ltd
26 Jan - 01 Feb Porter Airlines (Canada) Ltd
26 Jan - 02 Feb Porter Airlines (Canada) Ltd
26 Jan - 06 Feb Porter Airlines (Canada) Ltd
26 Jan - 09 Feb Porter Airlines (Canada) Ltd
29 Jan - 01 Feb Porter Airlines (Canada) Ltd
29 Jan - 02 Feb Porter Airlines (Canada) Ltd
29 Jan - 06 Feb Porter Airlines (Canada) Ltd
29 Jan - 09 Feb Porter Airlines (Canada) Ltd
12 Jan - 01 Feb Porter Airlines (Canada) Ltd
22 Jan - 01 Feb Porter Airlines (Canada) Ltd

Also check the deals for one-way flights from Montreal to Chicago in January.

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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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