Cheapest return flights from Toronto to Chicago in May from $136

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

Return flights

06 May - 10 May Porter Airlines (Canada) Ltd direct
07 May - 10 May Porter Airlines (Canada) Ltd direct
01 May - 03 May Air Transat direct
04 May - 23 May Porter Airlines (Canada) Ltd direct
04 May - 10 May Porter Airlines (Canada) Ltd direct
06 May - 23 May Porter Airlines (Canada) Ltd direct
07 May - 23 May Porter Airlines (Canada) Ltd direct
16 May - 23 May Porter Airlines (Canada) Ltd direct
01 May - 10 May Porter Airlines (Canada) Ltd direct
04 May - 22 May Porter Airlines (Canada) Ltd direct
28 May - 02 Jun Porter Airlines (Canada) Ltd direct
31 May - 17 Jun Porter Airlines (Canada) Ltd direct
31 May - 14 Jun Porter Airlines (Canada) Ltd direct
31 May - 07 Jun Porter Airlines (Canada) Ltd direct
29 May - 17 Jun Porter Airlines (Canada) Ltd direct
29 May - 14 Jun Porter Airlines (Canada) Ltd direct
29 May - 07 Jun 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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