Cheapest return flights from Chicago to Toronto in May from $169

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

Return flights

07 May - 10 May Porter Airlines (Canada) Ltd direct
11 May - 13 May Porter Airlines (Canada) Ltd direct
10 May - 13 May Porter Airlines (Canada) Ltd direct
15 May - 17 May Porter Airlines (Canada) Ltd direct
28 May - 31 May Porter Airlines (Canada) Ltd direct
28 May - 09 Jun Porter Airlines (Canada) Ltd direct
07 May - 09 May Porter Airlines (Canada) Ltd direct
12 May - 02 Jun Porter Airlines (Canada) Ltd direct
20 May - 04 Jun Porter Airlines (Canada) Ltd direct
20 May - 02 Jun Porter Airlines (Canada) Ltd direct
20 May - 03 Jun Porter Airlines (Canada) Ltd direct
20 May - 09 Jun Porter Airlines (Canada) Ltd direct
12 May - 23 May Porter Airlines (Canada) Ltd direct
07 May - 23 May Porter Airlines (Canada) Ltd direct
20 May - 23 May Porter Airlines (Canada) Ltd direct
01 May - 09 May Porter Airlines (Canada) Ltd direct
20 May - 07 Jun Porter Airlines (Canada) Ltd direct
20 May - 10 Jun Porter Airlines (Canada) Ltd direct
13 May - 02 Jun Porter Airlines (Canada) Ltd direct
13 May - 03 Jun Porter Airlines (Canada) Ltd direct

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

Powered by

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.