Cheapest return flights from Toronto to Chicago in September from 138€

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

Return flights

30 Sep - 06 Oct Air Canada direct
05 Sep - 08 Sep Air Canada direct
10 Sep - 10 Sep Air Canada direct
02 Sep - 05 Sep Air Canada direct
11 Sep - 12 Sep Air Canada direct
11 Sep - 18 Sep Air Canada direct
11 Sep - 11 Sep Air Canada direct
28 Sep - 05 Oct United direct
01 Sep - 10 Sep Air Canada direct
01 Sep - 06 Sep Air Canada direct
04 Sep - 06 Sep Air Canada direct
25 Sep - 30 Sep Air Canada direct

Also check the deals for one-way flights from Toronto 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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