Cheapest return flights from Chicago to Toronto in January from $340

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

Return flights

04 Jan - 15 Jan Porter Airlines (Canada) Ltd direct
04 Jan - 09 Jan Porter Airlines (Canada) Ltd direct
04 Jan - 06 Jan Porter Airlines (Canada) Ltd direct
01 Jan - 15 Jan Porter Airlines (Canada) Ltd direct
01 Jan - 09 Jan Porter Airlines (Canada) Ltd direct
01 Jan - 06 Jan Porter Airlines (Canada) Ltd direct
26 Jan - 30 Jan Porter Airlines (Canada) Ltd direct
15 Jan - 30 Jan Porter Airlines (Canada) Ltd direct
26 Jan - 09 Feb Porter Airlines (Canada) Ltd direct
01 Jan - 02 Jan Porter Airlines (Canada) Ltd direct
16 Jan - 30 Jan Porter Airlines (Canada) Ltd direct

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

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.