Cheapest return flights from Montreal to Chicago in May from $185

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

Return flights

06 May - 08 May Porter Airlines (Canada) Ltd
06 May - 11 May Porter Airlines (Canada) Ltd
06 May - 13 May Porter Airlines (Canada) Ltd
06 May - 25 May Porter Airlines (Canada) Ltd
06 May - 20 May Porter Airlines (Canada) Ltd
07 May - 08 May Porter Airlines (Canada) Ltd
07 May - 11 May Porter Airlines (Canada) Ltd
07 May - 13 May Porter Airlines (Canada) Ltd
07 May - 25 May Porter Airlines (Canada) Ltd
07 May - 20 May Porter Airlines (Canada) Ltd
11 May - 01 Jun Porter Airlines (Canada) Ltd
20 May - 01 Jun Porter Airlines (Canada) Ltd
20 May - 03 Jun Porter Airlines (Canada) Ltd
20 May - 04 Jun Porter Airlines (Canada) Ltd
21 May - 01 Jun Porter Airlines (Canada) Ltd
21 May - 03 Jun Porter Airlines (Canada) Ltd
21 May - 04 Jun Porter Airlines (Canada) Ltd
27 May - 01 Jun Porter Airlines (Canada) Ltd
27 May - 03 Jun Porter Airlines (Canada) Ltd
27 May - 04 Jun Porter Airlines (Canada) Ltd

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

Powered by

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.

Book a cheap hotel in Chicago

Cheap car rent in Chicago

Feel free to contact us with any feedback or request another flight research.