Cheapest return flights from Chicago to Toronto in May from $226

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

21 May - 28 May Porter Airlines (Canada) Ltd direct
23 May - 29 May Porter Airlines (Canada) Ltd direct
23 May - 30 May Porter Airlines (Canada) Ltd direct
16 May - 23 May Porter Airlines (Canada) Ltd direct
14 May - 19 May Porter Airlines (Canada) Ltd direct
16 May - 31 May Porter Airlines (Canada) Ltd direct
10 May - 12 May Porter Airlines (Canada) Ltd direct
08 May - 13 May Porter Airlines (Canada) Ltd direct
14 May - 21 May Porter Airlines (Canada) Ltd direct
06 May - 09 May Porter Airlines (Canada) Ltd direct
25 May - 01 Jun Porter Airlines (Canada) Ltd direct
13 May - 01 Jun Porter Airlines (Canada) Ltd direct
15 May - 01 Jun Porter Airlines (Canada) Ltd direct
27 May - 01 Jun Porter Airlines (Canada) Ltd direct
29 May - 01 Jun Porter Airlines (Canada) Ltd direct
11 May - 01 Jun Porter Airlines (Canada) Ltd direct
26 May - 01 Jun Porter Airlines (Canada) Ltd direct
21 May - 01 Jun Porter Airlines (Canada) Ltd direct
22 May - 01 Jun Porter Airlines (Canada) Ltd direct
31 May - 01 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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