Cheapest return flights from Toronto to Chicago in September from 139€

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

Return flights

18 Sep - 21 Sep Air Canada direct
15 Sep - 20 Sep Air Canada
04 Sep - 07 Sep Air Canada
23 Sep - 26 Sep Air Canada direct
15 Sep - 20 Sep Air Canada direct
15 Sep - 18 Sep Air Canada direct
05 Sep - 16 Sep Air Canada direct
12 Sep - 19 Sep Air Canada direct
17 Sep - 17 Sep Air Canada direct
13 Sep - 14 Sep Air Canada direct
26 Sep - 17 Oct Air Canada direct
15 Sep - 07 Oct Air Canada direct
04 Sep - 04 Oct Air Canada direct
04 Sep - 07 Oct Air Canada direct
29 Sep - 02 Oct Air Canada direct
30 Sep - 02 Oct Air Canada direct
25 Sep - 05 Oct Air Canada direct
30 Sep - 03 Oct 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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