Cheapest one-way flights from Toronto to Chicago in October from 94€

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

One-Way flights

12 Oct Porter Airlines (Canada) Ltd direct
03 Oct Porter Airlines (Canada) Ltd direct
30 Oct Porter Airlines (Canada) Ltd direct
08 Oct Porter Airlines (Canada) Ltd direct
19 Oct Porter Airlines (Canada) Ltd direct
06 Oct Porter Airlines (Canada) Ltd direct
22 Oct Porter Airlines (Canada) Ltd direct
20 Oct Porter Airlines (Canada) Ltd direct
26 Oct Porter Airlines (Canada) Ltd direct
28 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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