Cheapest one-way flights from Toronto to Chicago in September from $101

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

One-Way flights

26 Sep Porter Airlines (Canada) Ltd direct
30 Sep Porter Airlines (Canada) Ltd direct
29 Sep Porter Airlines (Canada) Ltd direct
28 Sep Porter Airlines (Canada) Ltd direct
27 Sep Porter Airlines (Canada) Ltd direct
24 Sep Porter Airlines (Canada) Ltd direct
21 Sep Porter Airlines (Canada) Ltd direct
23 Sep Porter Airlines (Canada) Ltd direct
20 Sep Porter Airlines (Canada) Ltd direct
22 Sep Porter Airlines (Canada) Ltd direct

Also check the deals for return flights from Toronto to Chicago 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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