Cheapest one-way flights from Toronto to Chicago in September from $87

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

One-Way flights

05 Sep Porter Airlines (Canada) Ltd direct
04 Sep Porter Airlines (Canada) Ltd direct
03 Sep Porter Airlines (Canada) Ltd direct
07 Sep Porter Airlines (Canada) Ltd direct
16 Sep Porter Airlines (Canada) Ltd direct
30 Sep Porter Airlines (Canada) Ltd direct
17 Sep Porter Airlines (Canada) Ltd direct
09 Sep Porter Airlines (Canada) Ltd direct
10 Sep Porter Airlines (Canada) Ltd direct
13 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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