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

Return flights

22 May - 24 May	United	direct
30 May - 01 Jun	United	direct
01 May - 09 May	United	direct
13 May - 17 May	United	direct
16 May - 18 May	United	direct
29 May - 30 May	United	direct
03 May - 10 May	United	direct
01 May - 02 May	United	direct
11 May - 15 May	Air Canada	direct
27 May - 06 Jun	United	direct
06 May - 10 Jun	United	direct
21 May - 24 May	Air Canada	direct
22 May - 25 May	Air Canada	direct

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

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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Cheapest return flights from Chicago to Toronto in May from $234

Return flights