Cheapest one-way flights from Toronto to Chicago in October from $100

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

One-Way flights

17 Oct Porter Airlines (Canada) Ltd direct
27 Oct Porter Airlines (Canada) Ltd direct
20 Oct Porter Airlines (Canada) Ltd direct
01 Oct Porter Airlines (Canada) Ltd direct
04 Oct Porter Airlines (Canada) Ltd direct
22 Oct Porter Airlines (Canada) Ltd direct
25 Oct Porter Airlines (Canada) Ltd direct
18 Oct Porter Airlines (Canada) Ltd direct
26 Oct Porter Airlines (Canada) Ltd direct
05 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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