Cheapest return flights from Toronto to Chicago in September from 122€

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

Return flights

21 Sep - 23 Sep Porter Airlines (Canada) Ltd direct
13 Sep - 15 Sep Porter Airlines (Canada) Ltd direct
07 Sep - 22 Sep Porter Airlines (Canada) Ltd direct
12 Sep - 14 Sep Porter Airlines (Canada) Ltd direct
26 Sep - 29 Sep Porter Airlines (Canada) Ltd direct
04 Sep - 08 Sep Porter Airlines (Canada) Ltd direct
05 Sep - 07 Sep Porter Airlines (Canada) Ltd direct
01 Sep - 08 Sep Porter Airlines (Canada) Ltd direct
01 Sep - 04 Sep Porter Airlines (Canada) Ltd direct
07 Sep - 15 Sep Porter Airlines (Canada) Ltd direct
13 Sep - 01 Oct Porter Airlines (Canada) Ltd direct
21 Sep - 06 Oct Porter Airlines (Canada) Ltd direct
21 Sep - 01 Oct Porter Airlines (Canada) Ltd direct
19 Sep - 06 Oct Porter Airlines (Canada) Ltd direct
19 Sep - 01 Oct Porter Airlines (Canada) Ltd direct
12 Sep - 01 Oct Porter Airlines (Canada) Ltd direct
16 Sep - 06 Oct Porter Airlines (Canada) Ltd direct
16 Sep - 01 Oct Porter Airlines (Canada) Ltd direct
28 Sep - 18 Oct Porter Airlines (Canada) Ltd direct
28 Sep - 06 Oct Porter Airlines (Canada) Ltd 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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