Cheapest return flights from Toronto to Chicago in October from $330

AirHint found the following cheapest return flights from Toronto (YTZ) to Chicago (MDW) in October 2026 (see full year).

Return flights

08 Oct - 12 Oct Porter Airlines (Canada) Ltd direct
03 Oct - 07 Oct Porter Airlines (Canada) Ltd direct
09 Oct - 11 Oct Porter Airlines (Canada) Ltd direct
09 Oct - 18 Oct Porter Airlines (Canada) Ltd direct
16 Oct - 18 Oct Porter Airlines (Canada) Ltd direct
14 Oct - 18 Oct Porter Airlines (Canada) Ltd direct
09 Oct - 13 Oct Porter Airlines (Canada) Ltd direct
09 Oct - 10 Oct Porter Airlines (Canada) Ltd direct
09 Oct - 09 Oct Porter Airlines (Canada) Ltd direct

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