Cheapest one-way flights from Toronto to Chicago in October from $88

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

One-Way flights

27 Oct Porter Airlines (Canada) Ltd direct
01 Oct Porter Airlines (Canada) Ltd direct
17 Oct Porter Airlines (Canada) Ltd direct
21 Oct Porter Airlines (Canada) Ltd direct
11 Oct Porter Airlines (Canada) Ltd direct
05 Oct Porter Airlines (Canada) Ltd direct
26 Oct Porter Airlines (Canada) Ltd direct
13 Oct Porter Airlines (Canada) Ltd direct
24 Oct Porter Airlines (Canada) Ltd direct
09 Oct Porter Airlines (Canada) Ltd direct

Also check the deals for return flights from Toronto to Chicago 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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