Cheapest return flights from Toronto to Chicago in July from $139

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

Return flights

21 Jul - 22 Jul Porter Airlines (Canada) Ltd direct
25 Jul - 27 Jul Porter Airlines (Canada) Ltd direct
20 Jul - 23 Jul Porter Airlines (Canada) Ltd direct
30 Jul - 15 Aug Porter Airlines (Canada) Ltd direct
26 Jul - 29 Jul Porter Airlines (Canada) Ltd direct
25 Jul - 30 Jul Porter Airlines (Canada) Ltd direct
26 Jul - 30 Jul Porter Airlines (Canada) Ltd direct
25 Jul - 29 Jul Porter Airlines (Canada) Ltd direct
26 Jul - 27 Jul Porter Airlines (Canada) Ltd direct
24 Jul - 30 Jul Porter Airlines (Canada) Ltd direct
29 Jul - 05 Aug Porter Airlines (Canada) Ltd direct
26 Jul - 03 Aug Porter Airlines (Canada) Ltd direct
25 Jul - 03 Aug Porter Airlines (Canada) Ltd direct
20 Jul - 02 Aug Porter Airlines (Canada) Ltd direct
23 Jul - 27 Jul Porter Airlines (Canada) Ltd direct
23 Jul - 09 Aug Porter Airlines (Canada) Ltd direct
23 Jul - 07 Aug Porter Airlines (Canada) Ltd direct
23 Jul - 06 Aug Porter Airlines (Canada) Ltd direct
24 Jul - 09 Aug Porter Airlines (Canada) Ltd direct
24 Jul - 07 Aug Porter Airlines (Canada) Ltd direct

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

Skyscanner

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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