Cheapest return flights from Toronto to Chicago in May from $186

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

Return flights

06 May - 09 May Porter Airlines (Canada) Ltd direct
07 May - 09 May Porter Airlines (Canada) Ltd direct
06 May - 17 May Porter Airlines (Canada) Ltd direct
27 May - 01 Jun Porter Airlines (Canada) Ltd direct
27 May - 13 Jun Porter Airlines (Canada) Ltd direct
07 May - 17 May Porter Airlines (Canada) Ltd direct
23 May - 01 Jun Porter Airlines (Canada) Ltd direct
23 May - 06 Jun Porter Airlines (Canada) Ltd direct
06 May - 15 May Porter Airlines (Canada) Ltd direct
07 May - 15 May Porter Airlines (Canada) Ltd direct
27 May - 06 Jun Porter Airlines (Canada) Ltd direct
27 May - 08 Jun Porter Airlines (Canada) Ltd direct
27 May - 15 Jun Porter Airlines (Canada) Ltd direct
27 May - 17 Jun Porter Airlines (Canada) Ltd direct
23 May - 08 Jun Porter Airlines (Canada) Ltd direct
14 May - 17 May Porter Airlines (Canada) Ltd direct
14 May - 01 Jun Porter Airlines (Canada) Ltd direct
14 May - 15 May Porter Airlines (Canada) Ltd direct

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