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

Return flights

01 May - 08 May	WestJet
02 May - 09 May	WestJet
04 May - 11 May	WestJet
05 May - 12 May	WestJet
06 May - 13 May	WestJet
07 May - 14 May	WestJet
10 May - 17 May	WestJet
12 May - 19 May	WestJet
16 May - 23 May	Delta

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

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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Cheapest return flights from Montreal to Chicago in May from 309€

Return flights