Cheapest return flights from Chicago to Toronto in September from $190

Best time to book flights for Chicago (MDW) to Toronto (YTZ) flights at AirHint

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

Return flights

15 Sep - 18 Sep Porter Airlines (Canada) Ltd direct
21 Sep - 23 Sep Porter Airlines (Canada) Ltd direct
05 Sep - 07 Sep Porter Airlines (Canada) Ltd direct
11 Sep - 13 Sep Porter Airlines (Canada) Ltd direct
19 Sep - 21 Sep Porter Airlines (Canada) Ltd direct
04 Sep - 11 Sep Porter Airlines (Canada) Ltd direct
05 Sep - 26 Sep Porter Airlines (Canada) Ltd direct
07 Sep - 08 Sep Porter Airlines (Canada) Ltd direct
07 Sep - 14 Sep Porter Airlines (Canada) Ltd direct
07 Sep - 25 Sep Porter Airlines (Canada) Ltd direct
18 Sep - 01 Oct Porter Airlines (Canada) Ltd direct
18 Sep - 08 Oct Porter Airlines (Canada) Ltd direct
18 Sep - 05 Oct Porter Airlines (Canada) Ltd direct
14 Sep - 01 Oct Porter Airlines (Canada) Ltd direct
14 Sep - 05 Oct Porter Airlines (Canada) Ltd direct
18 Sep - 02 Oct Porter Airlines (Canada) Ltd direct
14 Sep - 02 Oct Porter Airlines (Canada) Ltd direct
19 Sep - 02 Oct Porter Airlines (Canada) Ltd direct
19 Sep - 01 Oct Porter Airlines (Canada) Ltd direct
19 Sep - 08 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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