Cheapest return flights from Toronto to Chicago in February from $146

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

Return flights

08 Feb - 15 Feb Porter Airlines (Canada) Ltd direct
19 Feb - 24 Feb Porter Airlines (Canada) Ltd direct
11 Feb - 18 Feb Porter Airlines (Canada) Ltd direct
05 Feb - 22 Feb Porter Airlines (Canada) Ltd direct
13 Feb - 16 Feb Porter Airlines (Canada) Ltd direct
14 Feb - 22 Feb Porter Airlines (Canada) Ltd direct
19 Feb - 25 Feb Porter Airlines (Canada) Ltd direct
06 Feb - 08 Feb Porter Airlines (Canada) Ltd direct
20 Feb - 22 Feb Porter Airlines (Canada) Ltd direct
06 Feb - 09 Feb Porter Airlines (Canada) Ltd direct
27 Feb - 06 Mar Porter Airlines (Canada) Ltd direct
27 Feb - 02 Mar Porter Airlines (Canada) Ltd direct
20 Feb - 02 Mar Porter Airlines (Canada) Ltd direct
15 Feb - 06 Mar Porter Airlines (Canada) Ltd direct
15 Feb - 02 Mar Porter Airlines (Canada) Ltd direct
14 Feb - 06 Mar Porter Airlines (Canada) Ltd direct
14 Feb - 02 Mar Porter Airlines (Canada) Ltd direct
25 Feb - 06 Mar Porter Airlines (Canada) Ltd direct
25 Feb - 15 Mar Porter Airlines (Canada) Ltd direct
25 Feb - 08 Mar Porter Airlines (Canada) Ltd direct

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

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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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