Cheapest return flights from Toronto to Chicago in January from 285€

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

Return flights

01 Jan - 02 Jan Porter Airlines (Canada) Ltd direct
01 Jan - 01 Jan Porter Airlines (Canada) Ltd direct
01 Jan - 05 Jan Porter Airlines (Canada) Ltd direct
01 Jan - 11 Jan Porter Airlines (Canada) Ltd direct
08 Jan - 11 Jan Porter Airlines (Canada) Ltd direct

Also check the deals for one-way 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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