Cheapest return flights from Toronto to Chicago in August from $141

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

Return flights

19 Aug - 22 Aug Porter Airlines (Canada) Ltd direct
09 Aug - 10 Aug Porter Airlines (Canada) Ltd direct
03 Aug - 06 Aug Porter Airlines (Canada) Ltd direct
10 Aug - 12 Aug Porter Airlines (Canada) Ltd direct
07 Aug - 14 Aug Porter Airlines (Canada) Ltd direct
07 Aug - 10 Aug Porter Airlines (Canada) Ltd direct
13 Aug - 18 Aug Porter Airlines (Canada) Ltd direct
13 Aug - 17 Aug Porter Airlines (Canada) Ltd direct
05 Aug - 11 Aug Porter Airlines (Canada) Ltd direct
11 Aug - 14 Aug Porter Airlines (Canada) Ltd direct
26 Aug - 02 Sep Porter Airlines (Canada) Ltd direct
20 Aug - 08 Sep Porter Airlines (Canada) Ltd direct
20 Aug - 10 Sep Porter Airlines (Canada) Ltd direct
20 Aug - 09 Sep Porter Airlines (Canada) Ltd direct
20 Aug - 03 Sep Porter Airlines (Canada) Ltd direct
20 Aug - 04 Sep Porter Airlines (Canada) Ltd direct
20 Aug - 05 Sep Porter Airlines (Canada) Ltd direct
26 Aug - 08 Sep Porter Airlines (Canada) Ltd direct
26 Aug - 10 Sep Porter Airlines (Canada) Ltd direct
26 Aug - 09 Sep Porter Airlines (Canada) Ltd direct

Also check the deals for one-way 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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