Cheapest return flights from Chicago to Toronto in May from $330

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

Return flights

03 May - 10 May Porter Airlines (Canada) Ltd direct
01 May - 05 May Porter Airlines (Canada) Ltd direct
19 May - 21 May Porter Airlines (Canada) Ltd direct
18 May - 21 May Porter Airlines (Canada) Ltd direct
24 May - 04 Jun Porter Airlines (Canada) Ltd direct
24 May - 05 Jun Porter Airlines (Canada) Ltd direct
19 May - 04 Jun Porter Airlines (Canada) Ltd direct
19 May - 05 Jun Porter Airlines (Canada) Ltd direct
18 May - 04 Jun Porter Airlines (Canada) Ltd direct
18 May - 05 Jun Porter Airlines (Canada) Ltd direct
07 May - 12 May Porter Airlines (Canada) Ltd direct
30 May - 06 Jun Porter Airlines (Canada) Ltd direct
05 May - 17 May Porter Airlines (Canada) Ltd direct
05 May - 11 May Porter Airlines (Canada) Ltd direct
05 May - 15 May Porter Airlines (Canada) Ltd direct
05 May - 21 May Porter Airlines (Canada) Ltd direct
03 May - 17 May Porter Airlines (Canada) Ltd direct
24 May - 06 Jun Porter Airlines (Canada) Ltd direct
30 May - 04 Jun Porter Airlines (Canada) Ltd direct
30 May - 05 Jun Porter Airlines (Canada) Ltd direct

Also check the deals for one-way flights from Chicago to Toronto in May.

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