Cheapest one-way flights from Chicago to Toronto in October from $80

Best time to book flights for Chicago (MDW) to Toronto (YTZ) flights at AirHint

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

One-Way flights

08 Oct Porter Airlines (Canada) Ltd direct
27 Oct Porter Airlines (Canada) Ltd direct
31 Oct Porter Airlines (Canada) Ltd direct
01 Oct Porter Airlines (Canada) Ltd direct
15 Oct Porter Airlines (Canada) Ltd direct
11 Oct Porter Airlines (Canada) Ltd direct
12 Oct Porter Airlines (Canada) Ltd direct
14 Oct Porter Airlines (Canada) Ltd direct
10 Oct Porter Airlines (Canada) Ltd direct
13 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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