Cheapest return flights from Chicago to Toronto in October from $191

Best time to book flights for Chicago (MDW) to Toronto (YTZ) flights at AirHint

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

Return flights

05 Oct - 16 Oct Porter Airlines (Canada) Ltd direct
01 Oct - 06 Oct Porter Airlines (Canada) Ltd direct
03 Oct - 05 Oct Porter Airlines (Canada) Ltd direct
03 Oct - 07 Oct Porter Airlines (Canada) Ltd direct
04 Oct - 07 Oct Porter Airlines (Canada) Ltd direct
25 Oct - 26 Oct Porter Airlines (Canada) Ltd direct
25 Oct - 08 Nov Porter Airlines (Canada) Ltd direct
25 Oct - 04 Nov Porter Airlines (Canada) Ltd direct
25 Oct - 01 Nov Porter Airlines (Canada) Ltd direct
15 Oct - 26 Oct Porter Airlines (Canada) Ltd direct
15 Oct - 23 Oct Porter Airlines (Canada) Ltd direct
01 Oct - 08 Oct Porter Airlines (Canada) Ltd direct
01 Oct - 05 Oct Porter Airlines (Canada) Ltd direct
15 Oct - 04 Nov Porter Airlines (Canada) Ltd direct
15 Oct - 01 Nov Porter Airlines (Canada) Ltd direct
31 Oct - 08 Nov Porter Airlines (Canada) Ltd direct
31 Oct - 04 Nov Porter Airlines (Canada) Ltd direct
31 Oct - 01 Nov Porter Airlines (Canada) Ltd direct
16 Oct - 04 Nov Porter Airlines (Canada) Ltd direct
16 Oct - 01 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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