Cheapest return flights from Montreal to Chicago in May from 160€

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

Return flights

03 May - 05 May Porter Airlines (Canada) Ltd
03 May - 07 May Porter Airlines (Canada) Ltd
03 May - 08 May Porter Airlines (Canada) Ltd
03 May - 11 May Porter Airlines (Canada) Ltd
03 May - 13 May Porter Airlines (Canada) Ltd
03 May - 20 May Porter Airlines (Canada) Ltd
12 May - 13 May Porter Airlines (Canada) Ltd
12 May - 20 May Porter Airlines (Canada) Ltd
03 May - 04 May Porter Airlines (Canada) Ltd
03 May - 10 May Porter Airlines (Canada) Ltd
12 May - 01 Jun Porter Airlines (Canada) Ltd
12 May - 02 Jun Porter Airlines (Canada) Ltd
22 May - 01 Jun Porter Airlines (Canada) Ltd
22 May - 02 Jun Porter Airlines (Canada) Ltd
22 May - 03 Jun Porter Airlines (Canada) Ltd
22 May - 08 Jun Porter Airlines (Canada) Ltd
22 May - 05 Jun Porter Airlines (Canada) Ltd
22 May - 07 Jun Porter Airlines (Canada) Ltd
22 May - 09 Jun Porter Airlines (Canada) Ltd
23 May - 01 Jun Porter Airlines (Canada) Ltd

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