Cheapest return flights from Chicago to Toronto in September from $492

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

13 Sep - 25 Sep Porter Airlines (Canada) Ltd direct
04 Sep - 25 Sep Porter Airlines (Canada) Ltd direct
04 Sep - 11 Sep Porter Airlines (Canada) Ltd direct
01 Sep - 11 Sep Porter Airlines (Canada) Ltd direct
13 Sep - 15 Sep Porter Airlines (Canada) Ltd direct
04 Sep - 15 Sep Porter Airlines (Canada) Ltd direct
01 Sep - 15 Sep Porter Airlines (Canada) Ltd direct
11 Sep - 25 Sep Porter Airlines (Canada) Ltd direct
10 Sep - 25 Sep Porter Airlines (Canada) Ltd direct
10 Sep - 11 Sep 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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