Cheapest one-way flights from Toronto to Chicago in January from $82

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

One-Way flights

05 Jan Porter Airlines (Canada) Ltd direct
06 Jan Porter Airlines (Canada) Ltd direct
26 Jan Porter Airlines (Canada) Ltd direct
07 Jan Porter Airlines (Canada) Ltd direct
08 Jan Porter Airlines (Canada) Ltd direct
02 Jan Porter Airlines (Canada) Ltd direct
03 Jan Porter Airlines (Canada) Ltd direct
13 Jan Porter Airlines (Canada) Ltd direct
04 Jan Porter Airlines (Canada) Ltd direct
09 Jan Porter Airlines (Canada) Ltd direct

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

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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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