Cheapest return flights from Chicago to Toronto in May from $492

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

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

Return flights

27 May - 28 May Porter Airlines (Canada) Ltd direct
12 May - 19 May Porter Airlines (Canada) Ltd direct
12 May - 23 May Porter Airlines (Canada) Ltd direct
12 May - 28 May Porter Airlines (Canada) Ltd direct
12 May - 24 May Porter Airlines (Canada) Ltd direct
12 May - 20 May Porter Airlines (Canada) Ltd direct
22 May - 23 May Porter Airlines (Canada) Ltd direct
22 May - 28 May Porter Airlines (Canada) Ltd direct
22 May - 24 May Porter Airlines (Canada) Ltd direct
23 May - 28 May Porter Airlines (Canada) Ltd direct
27 May - 15 Jun Porter Airlines (Canada) Ltd direct
27 May - 05 Jun Porter Airlines (Canada) Ltd direct
27 May - 13 Jun Porter Airlines (Canada) Ltd direct
27 May - 11 Jun Porter Airlines (Canada) Ltd direct
22 May - 05 Jun Porter Airlines (Canada) Ltd direct
22 May - 11 Jun Porter Airlines (Canada) Ltd direct
28 May - 15 Jun Porter Airlines (Canada) Ltd direct
28 May - 05 Jun Porter Airlines (Canada) Ltd direct
28 May - 13 Jun Porter Airlines (Canada) Ltd direct
28 May - 11 Jun Porter Airlines (Canada) Ltd direct

Also check the deals for one-way 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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