Cheapest one-way flights from Toronto to Chicago in January from $103

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

One-Way flights

14 Jan Porter Airlines (Canada) Ltd direct
27 Jan Porter Airlines (Canada) Ltd direct
15 Jan Porter Airlines (Canada) Ltd direct
06 Jan Porter Airlines (Canada) Ltd direct
04 Jan Porter Airlines (Canada) Ltd direct

Also check the deals for return flights from Toronto to Chicago 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.

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