Cheapest one-way flights from Chicago to Toronto in September from $194

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

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

One-Way flights

15 Sep Porter Airlines (Canada) Ltd direct
27 Sep Porter Airlines (Canada) Ltd direct
21 Sep Porter Airlines (Canada) Ltd direct
22 Sep Porter Airlines (Canada) Ltd direct
26 Sep Porter Airlines (Canada) Ltd direct
18 Sep Porter Airlines (Canada) Ltd direct
29 Sep Air Transat direct
08 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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