Cheapest one-way flights from Toronto to Chicago in January from $109

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

One-Way flights

22 Jan Porter Airlines (Canada) Ltd direct
18 Jan Porter Airlines (Canada) Ltd direct
27 Jan Porter Airlines (Canada) Ltd direct
29 Jan Porter Airlines (Canada) Ltd direct
30 Jan Porter Airlines (Canada) Ltd direct
26 Jan Porter Airlines (Canada) Ltd direct
13 Jan Porter Airlines (Canada) Ltd direct
20 Jan Porter Airlines (Canada) Ltd direct
11 Jan Porter Airlines (Canada) Ltd direct
15 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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