Cheapest one-way flights from Chicago to Toronto in September from $73

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

One-Way flights

30 Sep Porter Airlines (Canada) Ltd direct
24 Sep Porter Airlines (Canada) Ltd direct
28 Sep Porter Airlines (Canada) Ltd direct
25 Sep Porter Airlines (Canada) Ltd direct
22 Sep Porter Airlines (Canada) Ltd direct
18 Sep Porter Airlines (Canada) Ltd direct
17 Sep Porter Airlines (Canada) Ltd direct
20 Sep Porter Airlines (Canada) Ltd direct
19 Sep Porter Airlines (Canada) Ltd direct
14 Sep Porter Airlines (Canada) Ltd direct

Also check the deals for return flights from Chicago to Toronto 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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