Cheapest return flights from Toronto to Chicago in January from $166

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

Return flights

25 Jan - 01 Feb Porter Airlines (Canada) Ltd direct
21 Jan - 03 Feb Porter Airlines (Canada) Ltd direct
22 Jan - 05 Feb Porter Airlines (Canada) Ltd direct
29 Jan - 02 Feb Porter Airlines (Canada) Ltd direct
15 Jan - 19 Jan Porter Airlines (Canada) Ltd direct
22 Jan - 25 Jan Porter Airlines (Canada) Ltd direct
22 Jan - 29 Jan Porter Airlines (Canada) Ltd direct
24 Jan - 31 Jan Porter Airlines (Canada) Ltd direct
23 Jan - 25 Jan Porter Airlines (Canada) Ltd direct
23 Jan - 26 Jan Porter Airlines (Canada) Ltd direct
19 Jan - 20 Jan Porter Airlines (Canada) Ltd direct
20 Jan - 25 Jan Porter Airlines (Canada) Ltd direct
11 Jan - 12 Jan Porter Airlines (Canada) Ltd direct
11 Jan - 18 Jan Porter Airlines (Canada) Ltd direct
25 Jan - 05 Feb Porter Airlines (Canada) Ltd direct
25 Jan - 12 Feb Porter Airlines (Canada) Ltd direct
25 Jan - 14 Feb Porter Airlines (Canada) Ltd direct
25 Jan - 06 Feb Porter Airlines (Canada) Ltd direct
16 Jan - 05 Feb Porter Airlines (Canada) Ltd direct
16 Jan - 01 Feb Porter Airlines (Canada) Ltd direct

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

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