Cheapest one-way flights from Chicago to Toronto in May from $70

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

One-Way flights

26 May Porter Airlines (Canada) Ltd direct
25 May Porter Airlines (Canada) Ltd direct
03 May Porter Airlines (Canada) Ltd direct
20 May Porter Airlines (Canada) Ltd direct
07 May Porter Airlines (Canada) Ltd direct
05 May Porter Airlines (Canada) Ltd direct
09 May Porter Airlines (Canada) Ltd direct
31 May Porter Airlines (Canada) Ltd direct
19 May Porter Airlines (Canada) Ltd direct
02 May Porter Airlines (Canada) Ltd direct

Also check the deals for return flights from Chicago to Toronto 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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