Cheapest return MDW–YUL flights, May

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

Return flights

25 May - 04 Jun Porter Airlines (Canada) Ltd
25 May - 12 Jun Porter Airlines (Canada) Ltd
25 May - 11 Jun Porter Airlines (Canada) Ltd
31 May - 04 Jun Porter Airlines (Canada) Ltd
31 May - 12 Jun Porter Airlines (Canada) Ltd
31 May - 11 Jun Porter Airlines (Canada) Ltd
31 May - 19 Jun Porter Airlines (Canada) Ltd
25 May - 27 May Porter Airlines (Canada) Ltd
25 May - 29 May Porter Airlines (Canada) Ltd
31 May - 18 Jun Porter Airlines (Canada) Ltd
25 May - 05 Jun Porter Airlines (Canada) Ltd
31 May - 05 Jun Porter Airlines (Canada) Ltd
25 May - 31 May Porter Airlines (Canada) Ltd
24 May - 26 May Delta
30 May - 31 May Delta
24 May - 28 May Delta
23 May - 26 May Delta
23 May - 24 May Delta
25 May - 26 May Porter Airlines (Canada) Ltd
24 May - 27 May Porter Airlines (Canada) Ltd

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

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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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