Cheapest one-way flights from Montreal to Chicago in October from $114

AirHint found the following cheapest one-way flights from Montreal (YUL) to Chicago (ORD) in October 2025 (see full year).

One-Way flights

06 Oct Air Canada direct
12 Oct Air Canada direct
29 Oct Air Canada direct
28 Oct Air Canada direct
24 Oct Air Canada direct
08 Oct Air Canada direct
16 Oct Air Canada direct
07 Oct Air Canada direct
11 Oct Air Canada direct
03 Oct Delta

Also check the deals for return flights from Montreal to Chicago in October.

Skyscanner

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.