Cheapest one-way flights from Toronto to Chicago in August from $171

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

One-Way flights

03 Aug Porter Airlines (Canada) Ltd direct
02 Aug Porter Airlines (Canada) Ltd direct
16 Aug Porter Airlines (Canada) Ltd direct
24 Aug Porter Airlines (Canada) Ltd direct
15 Aug Porter Airlines (Canada) Ltd direct
30 Aug Porter Airlines (Canada) Ltd direct
25 Aug Porter Airlines (Canada) Ltd direct
17 Aug Porter Airlines (Canada) Ltd direct
27 Aug Porter Airlines (Canada) Ltd direct

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

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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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