Cheapest return flights from Chicago to Toronto in August from $189

Best time to book flights for Chicago (MDW) to Toronto (YTZ) flights at AirHint

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

Return flights

27 Aug - 03 Sep Porter Airlines (Canada) Ltd direct
22 Aug - 24 Aug Porter Airlines (Canada) Ltd direct
15 Aug - 20 Aug Porter Airlines (Canada) Ltd direct
28 Aug - 31 Aug Porter Airlines (Canada) Ltd direct
21 Aug - 25 Aug Porter Airlines (Canada) Ltd direct
21 Aug - 22 Aug Porter Airlines (Canada) Ltd direct
21 Aug - 30 Aug Porter Airlines (Canada) Ltd direct
21 Aug - 26 Aug Porter Airlines (Canada) Ltd direct
21 Aug - 28 Aug Porter Airlines (Canada) Ltd direct
17 Aug - 22 Aug Porter Airlines (Canada) Ltd direct
17 Aug - 19 Aug Porter Airlines (Canada) Ltd direct
14 Aug - 02 Sep Porter Airlines (Canada) Ltd direct
14 Aug - 04 Sep Porter Airlines (Canada) Ltd direct
19 Aug - 02 Sep Porter Airlines (Canada) Ltd direct
19 Aug - 05 Sep Porter Airlines (Canada) Ltd direct
19 Aug - 04 Sep Porter Airlines (Canada) Ltd direct
24 Aug - 02 Sep Porter Airlines (Canada) Ltd direct
24 Aug - 05 Sep Porter Airlines (Canada) Ltd direct
24 Aug - 04 Sep Porter Airlines (Canada) Ltd direct
22 Aug - 02 Sep Porter Airlines (Canada) Ltd direct

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