Cheapest one-way flights from Toronto to Chicago in October from 75€

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

One-Way flights

18 Oct Porter Airlines (Canada) Ltd direct
07 Oct Porter Airlines (Canada) Ltd direct
19 Oct Porter Airlines (Canada) Ltd direct
17 Oct Air Transat direct
20 Oct Porter Airlines (Canada) Ltd direct
22 Oct Porter Airlines (Canada) Ltd direct
02 Oct Porter Airlines (Canada) Ltd direct
15 Oct Porter Airlines (Canada) Ltd direct
11 Oct Porter Airlines (Canada) Ltd direct
10 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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