Cheapest one-way flights from Chicago to Toronto in May from $77

Best time to book flights for Chicago (MDW) to Toronto (YTZ) flights at AirHint

AirHint found the following cheapest one-way flights from Chicago (MDW) to Toronto (YTZ) in May 2025 (see full year).

One-Way flights

30 May Porter Airlines (Canada) Ltd direct
27 May Porter Airlines (Canada) Ltd direct
25 May Porter Airlines (Canada) Ltd direct
26 May Porter Airlines (Canada) Ltd direct
23 May Porter Airlines (Canada) Ltd direct
24 May Porter Airlines (Canada) Ltd direct
20 May Porter Airlines (Canada) Ltd direct
19 May Porter Airlines (Canada) Ltd direct
16 May Porter Airlines (Canada) Ltd direct
18 May Porter Airlines (Canada) Ltd direct

Also check the deals for return 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