Cheapest return flights from Toronto to Chicago in August from $354

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

Return flights

07 Aug - 09 Aug Porter Airlines (Canada) Ltd direct
29 Aug - 16 Sep Porter Airlines (Canada) Ltd direct
07 Aug - 17 Aug Porter Airlines (Canada) Ltd direct
07 Aug - 16 Aug Porter Airlines (Canada) Ltd direct
07 Aug - 21 Aug Porter Airlines (Canada) Ltd direct
29 Aug - 02 Sep Porter Airlines (Canada) Ltd direct
23 Aug - 02 Sep Porter Airlines (Canada) Ltd direct
22 Aug - 02 Sep Porter Airlines (Canada) Ltd direct

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

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