Cheapest one-way flights from Chicago to Toronto in October from $73

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

One-Way flights

02 Oct Porter Airlines (Canada) Ltd direct
04 Oct Porter Airlines (Canada) Ltd direct
15 Oct Porter Airlines (Canada) Ltd direct
28 Oct Porter Airlines (Canada) Ltd direct
23 Oct Porter Airlines (Canada) Ltd direct
08 Oct Porter Airlines (Canada) Ltd direct
17 Oct Porter Airlines (Canada) Ltd direct
16 Oct Porter Airlines (Canada) Ltd direct
18 Oct Porter Airlines (Canada) Ltd direct
31 Oct Porter Airlines (Canada) Ltd direct

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

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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