Cheapest return flights from Toronto to Chicago in October from 122€

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

Return flights

15 Oct - 18 Oct Porter Airlines (Canada) Ltd direct
15 Oct - 31 Oct Porter Airlines (Canada) Ltd direct
20 Oct - 31 Oct Porter Airlines (Canada) Ltd direct
22 Oct - 31 Oct Porter Airlines (Canada) Ltd direct
02 Oct - 18 Oct Porter Airlines (Canada) Ltd direct
02 Oct - 06 Oct Porter Airlines (Canada) Ltd direct
02 Oct - 19 Oct Porter Airlines (Canada) Ltd direct
01 Oct - 18 Oct Porter Airlines (Canada) Ltd direct
01 Oct - 06 Oct Porter Airlines (Canada) Ltd direct
01 Oct - 01 Oct Porter Airlines (Canada) Ltd direct
15 Oct - 01 Nov Porter Airlines (Canada) Ltd direct
20 Oct - 08 Nov Porter Airlines (Canada) Ltd direct
20 Oct - 01 Nov Porter Airlines (Canada) Ltd direct
22 Oct - 08 Nov Porter Airlines (Canada) Ltd direct
22 Oct - 01 Nov Porter Airlines (Canada) Ltd direct
30 Oct - 16 Nov Porter Airlines (Canada) Ltd direct
30 Oct - 08 Nov Porter Airlines (Canada) Ltd direct
30 Oct - 14 Nov Porter Airlines (Canada) Ltd direct
30 Oct - 15 Nov Porter Airlines (Canada) Ltd direct
30 Oct - 01 Nov Porter Airlines (Canada) Ltd direct

Also check the deals for one-way 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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