Cheapest return flights from Chicago to Toronto in January from $148

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

Return flights

23 Jan - 29 Jan Porter Airlines (Canada) Ltd direct
21 Jan - 25 Jan Air Transat direct
23 Jan - 08 Feb Porter Airlines (Canada) Ltd direct
19 Jan - 29 Jan Porter Airlines (Canada) Ltd direct
23 Jan - 10 Feb Porter Airlines (Canada) Ltd direct
19 Jan - 08 Feb Porter Airlines (Canada) Ltd direct
09 Jan - 29 Jan Porter Airlines (Canada) Ltd direct
09 Jan - 16 Jan Porter Airlines (Canada) Ltd direct
10 Jan - 11 Jan Porter Airlines (Canada) Ltd direct
14 Jan - 18 Jan Porter Airlines (Canada) Ltd direct
01 Jan - 16 Jan Porter Airlines (Canada) Ltd direct
01 Jan - 09 Jan Porter Airlines (Canada) Ltd direct
11 Jan - 29 Jan Porter Airlines (Canada) Ltd direct
23 Jan - 13 Feb Porter Airlines (Canada) Ltd direct

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

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