Cheapest return flights from Toronto to Chicago in October from $136

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

Return flights

08 Oct - 15 Oct Porter Airlines (Canada) Ltd direct
02 Oct - 05 Oct Porter Airlines (Canada) Ltd direct
17 Oct - 21 Oct Porter Airlines (Canada) Ltd direct
15 Oct - 18 Oct Porter Airlines (Canada) Ltd direct
08 Oct - 09 Oct Porter Airlines (Canada) Ltd direct
08 Oct - 08 Oct Porter Airlines (Canada) Ltd direct
08 Oct - 21 Oct Porter Airlines (Canada) Ltd direct
08 Oct - 12 Oct Porter Airlines (Canada) Ltd direct
08 Oct - 22 Oct Porter Airlines (Canada) Ltd direct
05 Oct - 09 Oct Porter Airlines (Canada) Ltd direct
21 Oct - 05 Nov Porter Airlines (Canada) Ltd direct
21 Oct - 08 Nov Porter Airlines (Canada) Ltd direct
21 Oct - 06 Nov Porter Airlines (Canada) Ltd direct
21 Oct - 09 Nov Porter Airlines (Canada) Ltd direct
22 Oct - 05 Nov Porter Airlines (Canada) Ltd direct
22 Oct - 08 Nov Porter Airlines (Canada) Ltd direct
22 Oct - 06 Nov Porter Airlines (Canada) Ltd direct
22 Oct - 12 Nov Porter Airlines (Canada) Ltd direct
22 Oct - 09 Nov Porter Airlines (Canada) Ltd direct
28 Oct - 05 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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