Cheapest return flights from Toronto to Chicago in May from $232

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

Return flights

07 May - 12 May Porter Airlines (Canada) Ltd direct
08 May - 13 May Porter Airlines (Canada) Ltd direct
01 May - 31 May Porter Airlines (Canada) Ltd direct
08 May - 11 May Porter Airlines (Canada) Ltd direct
25 May - 29 May Porter Airlines (Canada) Ltd direct
23 May - 25 May Porter Airlines (Canada) Ltd direct
21 May - 25 May Porter Airlines (Canada) Ltd direct
07 May - 10 May Porter Airlines (Canada) Ltd direct
07 May - 13 May Porter Airlines (Canada) Ltd direct
07 May - 25 May Porter Airlines (Canada) Ltd direct
21 May - 07 Jun Porter Airlines (Canada) Ltd direct
25 May - 07 Jun Porter Airlines (Canada) Ltd direct
31 May - 07 Jun Porter Airlines (Canada) Ltd direct
26 May - 07 Jun Porter Airlines (Canada) Ltd direct
24 May - 07 Jun Porter Airlines (Canada) Ltd direct
21 May - 08 Jun Porter Airlines (Canada) Ltd direct
21 May - 03 Jun Porter Airlines (Canada) Ltd direct
25 May - 08 Jun Porter Airlines (Canada) Ltd direct
31 May - 08 Jun Porter Airlines (Canada) Ltd direct
31 May - 03 Jun Porter Airlines (Canada) Ltd direct

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

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