Cheapest return flights from Chicago to Toronto in October from $197

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

Return flights

15 Oct - 22 Oct Porter Airlines (Canada) Ltd direct
15 Oct - 17 Oct Porter Airlines (Canada) Ltd direct
02 Oct - 05 Oct Porter Airlines (Canada) Ltd direct
16 Oct - 19 Oct Porter Airlines (Canada) Ltd direct
17 Oct - 19 Oct Porter Airlines (Canada) Ltd direct
03 Oct - 08 Oct Porter Airlines (Canada) Ltd direct
18 Oct - 21 Oct Porter Airlines (Canada) Ltd direct
18 Oct - 26 Oct Porter Airlines (Canada) Ltd direct
19 Oct - 25 Oct Porter Airlines (Canada) Ltd direct
17 Oct - 20 Oct Porter Airlines (Canada) Ltd direct
31 Oct - 03 Nov Porter Airlines (Canada) Ltd direct
29 Oct - 04 Nov Porter Airlines (Canada) Ltd direct
29 Oct - 03 Nov Porter Airlines (Canada) Ltd direct
31 Oct - 12 Nov Porter Airlines (Canada) Ltd direct
31 Oct - 06 Nov Porter Airlines (Canada) Ltd direct
31 Oct - 14 Nov Porter Airlines (Canada) Ltd direct
31 Oct - 20 Nov Porter Airlines (Canada) Ltd direct
31 Oct - 11 Nov Porter Airlines (Canada) Ltd direct
31 Oct - 05 Nov Porter Airlines (Canada) Ltd direct
31 Oct - 07 Nov Porter Airlines (Canada) Ltd direct

Also check the deals for one-way flights from Chicago to Toronto in October.

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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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