Cheapest return flights from Chicago to Toronto in May from 177€

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

Return flights

09 May - 22 May Porter Airlines (Canada) Ltd direct
09 May - 27 May Porter Airlines (Canada) Ltd direct
09 May - 23 May Porter Airlines (Canada) Ltd direct
30 May - 18 Jun Porter Airlines (Canada) Ltd direct
30 May - 04 Jun Porter Airlines (Canada) Ltd direct
15 May - 23 May Porter Airlines (Canada) Ltd direct
15 May - 22 May Porter Airlines (Canada) Ltd direct
15 May - 27 May Porter Airlines (Canada) Ltd direct
15 May - 04 Jun Porter Airlines (Canada) Ltd direct

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

Book a cheap hotel in Toronto

Cheap car rent in Toronto

Feel free to contact us with any feedback or request another flight research.