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

Return flights

01 May - 08 May	Avianca
02 May - 09 May	Avianca
03 May - 10 May	Avianca
05 May - 12 May	Avianca
07 May - 14 May	Avianca
09 May - 16 May	Avianca
20 May - 27 May	Avianca
21 May - 28 May	Avianca
23 May - 30 May	Avianca
24 May - 31 May	WestJet
26 May - 02 Jun	Avianca
29 May - 05 Jun	WestJet
27 May - 03 Jun	United	direct
28 May - 04 Jun	United	direct
29 May - 05 Jun	United	direct
30 May - 06 Jun	Air Canada	direct
31 May - 07 Jun	WestJet
31 May - 07 Jun	United	direct
25 May - 01 Jun	Air Canada	direct

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 $313

Return flights