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

Return flights

15 Jan - 24 Jan	WestJet
16 Jan - 24 Jan	WestJet
19 Jan - 23 Jan	WestJet
17 Jan - 20 Jan	WestJet
28 Jan - 02 Feb	WestJet
15 Jan - 24 Jan	United	direct
16 Jan - 24 Jan	United	direct
28 Jan - 02 Feb	United	direct
19 Jan - 23 Jan	Air Canada	direct
17 Jan - 20 Jan	Air Canada	direct

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

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 Toronto to Chicago in January from 223€

Return flights