Cheapest return flights from Chicago to Toronto in September from $195

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

Return flights

25 Sep - 28 Sep Porter Airlines (Canada) Ltd direct
27 Sep - 29 Sep Porter Airlines (Canada) Ltd direct
26 Sep - 30 Sep Porter Airlines (Canada) Ltd direct
25 Sep - 29 Sep Porter Airlines (Canada) Ltd direct
25 Sep - 30 Sep Porter Airlines (Canada) Ltd direct
26 Sep - 29 Sep Porter Airlines (Canada) Ltd direct
30 Sep - 19 Oct Porter Airlines (Canada) Ltd direct
24 Sep - 28 Sep Porter Airlines (Canada) Ltd direct
23 Sep - 30 Sep Porter Airlines (Canada) Ltd direct
23 Sep - 29 Sep Porter Airlines (Canada) Ltd direct
23 Sep - 24 Sep Porter Airlines (Canada) Ltd direct
23 Sep - 12 Oct Porter Airlines (Canada) Ltd direct
23 Sep - 04 Oct Porter Airlines (Canada) Ltd direct
23 Sep - 07 Oct Porter Airlines (Canada) Ltd direct
23 Sep - 08 Oct Porter Airlines (Canada) Ltd direct
23 Sep - 01 Oct Porter Airlines (Canada) Ltd direct
23 Sep - 02 Oct Porter Airlines (Canada) Ltd direct
28 Sep - 12 Oct Porter Airlines (Canada) Ltd direct
28 Sep - 18 Oct Porter Airlines (Canada) Ltd direct
28 Sep - 04 Oct Porter Airlines (Canada) Ltd direct

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

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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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