Cheapest one-way flights from Toronto to Chicago in August from $89

AirHint found the following cheapest one-way flights from Toronto (YTZ) to Chicago (MDW) in August 2025 (see full year).

One-Way flights

05 Aug Porter Airlines (Canada) Ltd direct
25 Aug Porter Airlines (Canada) Ltd direct
19 Aug Porter Airlines (Canada) Ltd direct
06 Aug Porter Airlines (Canada) Ltd direct
21 Aug Porter Airlines (Canada) Ltd direct
16 Aug Porter Airlines (Canada) Ltd direct
17 Aug Porter Airlines (Canada) Ltd direct
03 Aug Porter Airlines (Canada) Ltd direct
24 Aug Porter Airlines (Canada) Ltd direct
20 Aug Porter Airlines (Canada) Ltd direct

Also check the deals for return flights from Toronto to Chicago in August.

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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