Cheapest return flights from Montreal to Chicago in October from $382

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

Return flights

31 Oct - 07 Nov Air Transat
30 Oct - 20 Nov Porter Airlines (Canada) Ltd
29 Oct - 05 Nov Porter Airlines (Canada) Ltd
30 Oct - 12 Nov Porter Airlines (Canada) Ltd
30 Oct - 11 Nov Porter Airlines (Canada) Ltd
30 Oct - 17 Nov Porter Airlines (Canada) Ltd
30 Oct - 16 Nov Porter Airlines (Canada) Ltd
30 Oct - 06 Nov Porter Airlines (Canada) Ltd
28 Oct - 04 Nov Porter Airlines (Canada) Ltd
30 Oct - 14 Nov Porter Airlines (Canada) Ltd
28 Oct - 31 Oct Porter Airlines (Canada) Ltd
29 Oct - 30 Oct Delta
30 Oct - 31 Oct Porter Airlines (Canada) Ltd
24 Oct - 31 Oct Porter Airlines (Canada) Ltd
28 Oct - 28 Oct Porter Airlines (Canada) Ltd
23 Oct - 31 Oct Porter Airlines (Canada) Ltd
23 Oct - 24 Oct Porter Airlines (Canada) Ltd
23 Oct - 28 Oct Porter Airlines (Canada) Ltd
23 Oct - 29 Oct Porter Airlines (Canada) Ltd
27 Oct - 28 Oct Porter Airlines (Canada) Ltd

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

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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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