Cheapest return flights from Montreal to Chicago in October from $181

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

Return flights

01 Oct - 08 Oct Air Canada direct
02 Oct - 09 Oct Air Canada direct
03 Oct - 10 Oct Air Canada direct
04 Oct - 11 Oct Air Canada direct
05 Oct - 12 Oct Air Canada direct
08 Oct - 15 Oct Air Canada direct
11 Oct - 18 Oct Air Canada direct
12 Oct - 19 Oct Air Canada direct
13 Oct - 20 Oct Air Canada direct
14 Oct - 21 Oct Air Canada direct
25 Oct - 01 Nov Air Canada direct
26 Oct - 02 Nov Air Canada direct
27 Oct - 03 Nov Air Canada direct
28 Oct - 04 Nov Air Canada direct
29 Oct - 05 Nov Air Canada direct
30 Oct - 06 Nov Air Canada direct
31 Oct - 05 Nov Air Canada direct
31 Oct - 07 Nov Air Canada direct

Also check the deals for one-way 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.

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