Cheapest one-way flights from Toronto to Chicago in February from $86

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

One-Way flights

18 Feb Porter Airlines (Canada) Ltd direct
10 Feb Porter Airlines (Canada) Ltd direct
06 Feb Porter Airlines (Canada) Ltd direct
25 Feb Porter Airlines (Canada) Ltd direct
12 Feb Porter Airlines (Canada) Ltd direct
13 Feb Porter Airlines (Canada) Ltd direct
14 Feb Porter Airlines (Canada) Ltd direct
16 Feb Porter Airlines (Canada) Ltd direct
15 Feb Porter Airlines (Canada) Ltd direct

Also check the deals for return 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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