Cheapest one-way flights from Toronto to Chicago in May from $105

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

One-Way flights

27 May Porter Airlines (Canada) Ltd direct
13 May Porter Airlines (Canada) Ltd direct
25 May Porter Airlines (Canada) Ltd direct
21 May Porter Airlines (Canada) Ltd direct
23 May Porter Airlines (Canada) Ltd direct
07 May Porter Airlines (Canada) Ltd direct
04 May Porter Airlines (Canada) Ltd direct
18 May Porter Airlines (Canada) Ltd direct

Also check the deals for return flights from Toronto to Chicago in May.

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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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