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

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

Return flights

16 Sep - 20 Sep Porter Airlines (Canada) Ltd direct
22 Sep - 23 Sep Porter Airlines (Canada) Ltd direct
19 Sep - 25 Sep Porter Airlines (Canada) Ltd direct
13 Sep - 25 Sep Porter Airlines (Canada) Ltd direct
13 Sep - 23 Sep Porter Airlines (Canada) Ltd direct
13 Sep - 20 Sep Porter Airlines (Canada) Ltd direct
10 Sep - 25 Sep Porter Airlines (Canada) Ltd direct
10 Sep - 23 Sep Porter Airlines (Canada) Ltd direct
10 Sep - 20 Sep Porter Airlines (Canada) Ltd direct
19 Sep - 23 Sep Porter Airlines (Canada) Ltd direct
30 Sep - 12 Oct Porter Airlines (Canada) Ltd direct
30 Sep - 11 Oct Porter Airlines (Canada) Ltd direct
30 Sep - 18 Oct Porter Airlines (Canada) Ltd direct
22 Sep - 12 Oct Porter Airlines (Canada) Ltd direct
22 Sep - 11 Oct Porter Airlines (Canada) Ltd direct
26 Sep - 12 Oct Porter Airlines (Canada) Ltd direct
26 Sep - 11 Oct Porter Airlines (Canada) Ltd direct
30 Sep - 08 Oct Porter Airlines (Canada) Ltd direct
30 Sep - 13 Oct Porter Airlines (Canada) Ltd direct
30 Sep - 10 Oct Porter Airlines (Canada) Ltd direct

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

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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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