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

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

Return flights

26 Sep - 28 Sep Air Canada direct
23 Sep - 29 Sep Air Canada direct
12 Sep - 23 Sep Air Canada direct
12 Sep - 20 Sep Air Canada direct
18 Sep - 21 Sep Air Canada direct
02 Sep - 09 Sep Air Canada direct
03 Sep - 10 Sep Air Canada direct
04 Sep - 11 Sep Air Canada direct
06 Sep - 13 Sep Air Canada direct
07 Sep - 14 Sep Air Canada direct
25 Sep - 01 Oct Air Canada direct
26 Sep - 01 Oct Air Canada direct
25 Sep - 02 Oct Air Canada direct
26 Sep - 03 Oct Air Canada direct
27 Sep - 04 Oct Air Canada direct
29 Sep - 06 Oct Air Canada direct
30 Sep - 07 Oct Air Canada direct
24 Sep - 01 Oct Air Canada direct
28 Sep - 05 Oct Air Canada direct

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

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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