Cheapest one-way flights from Toronto to Chicago in September from 75€

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

One-Way flights

15 Sep Porter Airlines (Canada) Ltd direct
14 Sep Porter Airlines (Canada) Ltd direct
12 Sep Porter Airlines (Canada) Ltd direct
01 Sep Porter Airlines (Canada) Ltd direct
18 Sep Porter Airlines (Canada) Ltd direct
02 Sep Porter Airlines (Canada) Ltd direct
24 Sep Air Transat direct
04 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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