Cheapest return flights from Montreal to Chicago in May from $187

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 United direct
02 May - 09 May Air Canada direct
05 May - 12 May Air Canada direct
09 May - 16 May United direct
23 May - 30 May Air Canada direct
20 May - 27 May United direct
27 May - 03 Jun United direct
24 May - 31 May United
12 May - 20 May United
13 May - 20 May United
26 May - 02 Jun United
22 May - 27 May Delta
28 May - 04 Jun Air Canada direct
30 May - 06 Jun Air Canada direct
26 May - 02 Jun Air Canada direct
31 May - 07 Jun Porter Airlines (Canada) Ltd direct
29 May - 05 Jun WestJet
29 May - 05 Jun Porter Airlines (Canada) Ltd direct
25 May - 01 Jun WestJet
25 May - 01 Jun Porter Airlines (Canada) Ltd direct

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.