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

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

Return flights

03 Sep - 07 Sep Porter Airlines (Canada) Ltd direct
12 Sep - 14 Sep Porter Airlines (Canada) Ltd direct
11 Sep - 25 Sep Porter Airlines (Canada) Ltd direct
17 Sep - 19 Sep Porter Airlines (Canada) Ltd direct
22 Sep - 24 Sep Porter Airlines (Canada) Ltd direct
10 Sep - 13 Sep Porter Airlines (Canada) Ltd direct
23 Sep - 30 Sep Porter Airlines (Canada) Ltd direct
04 Sep - 10 Sep Porter Airlines (Canada) Ltd direct
13 Sep - 17 Sep Porter Airlines (Canada) Ltd direct
23 Sep - 25 Sep Porter Airlines (Canada) Ltd direct
23 Sep - 06 Oct Porter Airlines (Canada) Ltd direct
23 Sep - 07 Oct Porter Airlines (Canada) Ltd direct
18 Sep - 06 Oct Porter Airlines (Canada) Ltd direct
18 Sep - 07 Oct Porter Airlines (Canada) Ltd direct
21 Sep - 06 Oct Porter Airlines (Canada) Ltd direct
21 Sep - 07 Oct Porter Airlines (Canada) Ltd direct
30 Sep - 06 Oct Porter Airlines (Canada) Ltd direct
30 Sep - 07 Oct Porter Airlines (Canada) Ltd direct
29 Sep - 06 Oct Porter Airlines (Canada) Ltd direct
29 Sep - 07 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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