Cheapest return flights from Chicago to Toronto in January from $174

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

Return flights

28 Jan - 02 Feb Porter Airlines (Canada) Ltd direct
29 Jan - 02 Feb Porter Airlines (Canada) Ltd direct
20 Jan - 27 Jan Porter Airlines (Canada) Ltd direct
29 Jan - 01 Feb Porter Airlines (Canada) Ltd direct
22 Jan - 28 Jan Porter Airlines (Canada) Ltd direct
24 Jan - 31 Jan Porter Airlines (Canada) Ltd direct
22 Jan - 26 Jan Porter Airlines (Canada) Ltd direct
23 Jan - 02 Feb Porter Airlines (Canada) Ltd direct
23 Jan - 05 Feb Porter Airlines (Canada) Ltd direct
20 Jan - 02 Feb Porter Airlines (Canada) Ltd direct
20 Jan - 05 Feb Porter Airlines (Canada) Ltd direct
30 Jan - 14 Feb Porter Airlines (Canada) Ltd direct
30 Jan - 20 Feb Porter Airlines (Canada) Ltd direct
30 Jan - 16 Feb Porter Airlines (Canada) Ltd direct
19 Jan - 21 Jan Porter Airlines (Canada) Ltd direct
17 Jan - 20 Jan Porter Airlines (Canada) Ltd direct
17 Jan - 21 Jan Porter Airlines (Canada) Ltd direct
17 Jan - 26 Jan Porter Airlines (Canada) Ltd direct
23 Jan - 25 Jan Porter Airlines (Canada) Ltd direct
23 Jan - 29 Jan Porter Airlines (Canada) Ltd direct

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

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