Cheapest return flights from Toronto to Chicago in September from $136

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

Return flights

07 Sep - 11 Sep Porter Airlines (Canada) Ltd direct
13 Sep - 14 Sep Porter Airlines (Canada) Ltd direct
20 Sep - 21 Sep Porter Airlines (Canada) Ltd direct
14 Sep - 16 Sep Porter Airlines (Canada) Ltd direct
19 Sep - 22 Sep Porter Airlines (Canada) Ltd direct
19 Sep - 21 Sep Porter Airlines (Canada) Ltd direct
20 Sep - 23 Sep Porter Airlines (Canada) Ltd direct
05 Sep - 07 Sep Porter Airlines (Canada) Ltd direct
18 Sep - 21 Sep Porter Airlines (Canada) Ltd direct
26 Sep - 30 Sep Porter Airlines (Canada) Ltd direct
29 Sep - 01 Oct Porter Airlines (Canada) Ltd direct
26 Sep - 03 Oct Porter Airlines (Canada) Ltd direct
23 Sep - 09 Oct Porter Airlines (Canada) Ltd direct
23 Sep - 04 Oct Porter Airlines (Canada) Ltd direct
23 Sep - 01 Oct Porter Airlines (Canada) Ltd direct
23 Sep - 08 Oct Porter Airlines (Canada) Ltd direct
23 Sep - 12 Oct Porter Airlines (Canada) Ltd direct
25 Sep - 09 Oct Porter Airlines (Canada) Ltd direct
25 Sep - 04 Oct Porter Airlines (Canada) Ltd direct
25 Sep - 01 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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