Cheapest return flights from Chicago to Toronto in January from $531

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

Return flights

30 Jan - 17 Feb Porter Airlines (Canada) Ltd direct
30 Jan - 18 Feb Porter Airlines (Canada) Ltd direct
30 Jan - 19 Feb Porter Airlines (Canada) Ltd direct
29 Jan - 17 Feb Porter Airlines (Canada) Ltd direct
29 Jan - 19 Feb Porter Airlines (Canada) Ltd direct
29 Jan - 18 Feb Porter Airlines (Canada) Ltd direct
30 Jan - 12 Feb Porter Airlines (Canada) Ltd direct
29 Jan - 12 Feb Porter Airlines (Canada) Ltd direct
30 Jan - 06 Feb Porter Airlines (Canada) Ltd direct
29 Jan - 08 Feb Porter Airlines (Canada) Ltd direct

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

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