Cheapest return flights from Chicago to Toronto in October from $342

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

Return flights

31 Oct - 19 Nov Porter Airlines (Canada) Ltd direct
31 Oct - 18 Nov Porter Airlines (Canada) Ltd direct
31 Oct - 12 Nov Porter Airlines (Canada) Ltd direct
31 Oct - 10 Nov Porter Airlines (Canada) Ltd direct
31 Oct - 13 Nov Porter Airlines (Canada) Ltd direct
31 Oct - 09 Nov Porter Airlines (Canada) Ltd direct
31 Oct - 16 Nov Porter Airlines (Canada) Ltd direct
31 Oct - 17 Nov Porter Airlines (Canada) Ltd direct
31 Oct - 20 Nov Porter Airlines (Canada) Ltd direct
31 Oct - 03 Nov Frontier Airlines
28 Oct - 29 Oct Porter Airlines (Canada) Ltd direct
28 Oct - 30 Oct Porter Airlines (Canada) Ltd direct
29 Oct - 30 Oct Porter Airlines (Canada) Ltd direct
26 Oct - 28 Oct Porter Airlines (Canada) Ltd direct
26 Oct - 30 Oct Porter Airlines (Canada) Ltd direct
27 Oct - 28 Oct Porter Airlines (Canada) Ltd direct
27 Oct - 30 Oct Porter Airlines (Canada) Ltd direct
27 Oct - 29 Oct Porter Airlines (Canada) Ltd direct
21 Oct - 28 Oct Porter Airlines (Canada) Ltd direct
21 Oct - 30 Oct Porter Airlines (Canada) Ltd direct

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

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