Cheapest one-way flights from Chicago to Toronto in May from $96

Best time to book flights for Chicago (MDW) to Toronto (YTZ) flights at AirHint

AirHint found the following cheapest one-way flights from Chicago (MDW) to Toronto (YTZ) in May 2025 (see full year).

One-Way flights

16 May Porter Airlines (Canada) Ltd direct
21 May Porter Airlines (Canada) Ltd direct
11 May Porter Airlines (Canada) Ltd direct
27 May Porter Airlines (Canada) Ltd direct
10 May Porter Airlines (Canada) Ltd direct
12 May Porter Airlines (Canada) Ltd direct
22 May Porter Airlines (Canada) Ltd direct
18 May Porter Airlines (Canada) Ltd direct
04 May Porter Airlines (Canada) Ltd direct
25 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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