Cheapest return flights from Toronto to Chicago in August from $330

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

Return flights

13 Aug - 18 Aug Porter Airlines (Canada) Ltd direct
22 Aug - 12 Sep Porter Airlines (Canada) Ltd direct
16 Aug - 18 Aug Porter Airlines (Canada) Ltd direct
02 Aug - 18 Aug Porter Airlines (Canada) Ltd direct
20 Aug - 27 Aug Porter Airlines (Canada) Ltd direct
13 Aug - 27 Aug Porter Airlines (Canada) Ltd direct
13 Aug - 14 Aug Porter Airlines (Canada) Ltd direct
25 Aug - 27 Aug Porter Airlines (Canada) Ltd direct
16 Aug - 27 Aug Porter Airlines (Canada) Ltd direct
24 Aug - 27 Aug Porter Airlines (Canada) Ltd direct
21 Aug - 27 Aug Porter Airlines (Canada) Ltd direct
20 Aug - 03 Sep Porter Airlines (Canada) Ltd direct
13 Aug - 03 Sep Porter Airlines (Canada) Ltd direct
25 Aug - 03 Sep Porter Airlines (Canada) Ltd direct
25 Aug - 15 Sep Porter Airlines (Canada) Ltd direct
16 Aug - 03 Sep Porter Airlines (Canada) Ltd direct
30 Aug - 03 Sep Porter Airlines (Canada) Ltd direct
30 Aug - 15 Sep Porter Airlines (Canada) Ltd direct
24 Aug - 03 Sep Porter Airlines (Canada) Ltd direct
21 Aug - 03 Sep Porter Airlines (Canada) Ltd direct

Also check the deals for one-way 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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