Cheapest one-way flights from Toronto to Chicago in September from $183

AirHint found the following cheapest one-way flights from Toronto (YTZ) to Chicago (MDW) in September 2026 (see full year).

One-Way flights

10 Sep Porter Airlines (Canada) Ltd direct
13 Sep Porter Airlines (Canada) Ltd direct
30 Sep Porter Airlines (Canada) Ltd direct
19 Sep Porter Airlines (Canada) Ltd direct
22 Sep Porter Airlines (Canada) Ltd direct
26 Sep Porter Airlines (Canada) Ltd direct

Also check the deals for return flights from Toronto to Chicago in September.

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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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