Cheapest return flights from Toronto to Chicago in October from $160

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

Return flights

17 Oct - 19 Oct Porter Airlines (Canada) Ltd direct
08 Oct - 18 Oct Porter Airlines (Canada) Ltd direct
17 Oct - 31 Oct Porter Airlines (Canada) Ltd direct
01 Oct - 05 Oct Porter Airlines (Canada) Ltd direct
18 Oct - 22 Oct Porter Airlines (Canada) Ltd direct
03 Oct - 06 Oct Porter Airlines (Canada) Ltd direct
02 Oct - 05 Oct Porter Airlines (Canada) Ltd direct
12 Oct - 22 Nov Porter Airlines (Canada) Ltd direct
15 Oct - 22 Nov Porter Airlines (Canada) Ltd direct
17 Oct - 20 Oct Porter Airlines (Canada) Ltd direct
08 Oct - 14 Oct Porter Airlines (Canada) Ltd direct
01 Oct - 04 Oct Porter Airlines (Canada) Ltd direct
26 Oct - 04 Nov Porter Airlines (Canada) Ltd direct
24 Oct - 09 Nov Porter Airlines (Canada) Ltd direct
20 Oct - 09 Nov Porter Airlines (Canada) Ltd direct
20 Oct - 04 Nov Porter Airlines (Canada) Ltd direct
22 Oct - 09 Nov Porter Airlines (Canada) Ltd direct
22 Oct - 12 Nov Porter Airlines (Canada) Ltd direct
22 Oct - 04 Nov Porter Airlines (Canada) Ltd direct
22 Oct - 11 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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