Cheapest return flights from Toronto to Chicago in May from 291€

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

Return flights

02 May - 06 May Porter Airlines (Canada) Ltd direct
02 May - 22 May Porter Airlines (Canada) Ltd direct
22 May - 22 May Porter Airlines (Canada) Ltd direct
22 May - 06 Jun Porter Airlines (Canada) Ltd direct
22 May - 05 Jun Porter Airlines (Canada) Ltd direct
22 May - 12 Jun Porter Airlines (Canada) Ltd direct

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

Skyscanner

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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