Cheapest return flights from Toronto to Chicago in July from $333

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

Return flights

06 Jul - 16 Jul Porter Airlines (Canada) Ltd direct
06 Jul - 08 Jul Porter Airlines (Canada) Ltd direct
14 Jul - 16 Jul Porter Airlines (Canada) Ltd direct
08 Jul - 08 Jul Porter Airlines (Canada) Ltd direct
08 Jul - 16 Jul Porter Airlines (Canada) Ltd direct
16 Jul - 16 Jul Porter Airlines (Canada) Ltd direct
31 Jul - 18 Aug Porter Airlines (Canada) Ltd direct
06 Jul - 07 Jul Porter Airlines (Canada) Ltd direct
06 Jul - 27 Jul Porter Airlines (Canada) Ltd direct
06 Jul - 06 Jul Porter Airlines (Canada) Ltd direct
14 Jul - 27 Jul Porter Airlines (Canada) Ltd direct
14 Jul - 01 Aug Porter Airlines (Canada) Ltd direct
31 Jul - 10 Aug Porter Airlines (Canada) Ltd direct
31 Jul - 01 Aug Porter Airlines (Canada) Ltd direct
31 Jul - 14 Aug Porter Airlines (Canada) Ltd direct
31 Jul - 11 Aug Porter Airlines (Canada) Ltd direct
31 Jul - 08 Aug Porter Airlines (Canada) Ltd direct
16 Jul - 01 Aug Porter Airlines (Canada) Ltd direct

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

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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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