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

21 Jan - 22 Jan Porter Airlines (Canada) Ltd direct
15 Jan - 22 Jan Porter Airlines (Canada) Ltd direct
29 Jan - 08 Feb Porter Airlines (Canada) Ltd direct
30 Jan - 08 Feb Porter Airlines (Canada) Ltd direct
27 Jan - 08 Feb Porter Airlines (Canada) Ltd direct
21 Jan - 08 Feb Porter Airlines (Canada) Ltd direct
09 Jan - 22 Jan Porter Airlines (Canada) Ltd direct
11 Jan - 22 Jan Porter Airlines (Canada) Ltd direct
15 Jan - 15 Jan Porter Airlines (Canada) Ltd direct
30 Jan - 03 Feb Porter Airlines (Canada) Ltd direct
30 Jan - 01 Feb Porter Airlines (Canada) Ltd direct
15 Jan - 03 Feb Porter Airlines (Canada) Ltd direct
15 Jan - 01 Feb Porter Airlines (Canada) Ltd direct
27 Jan - 03 Feb Porter Airlines (Canada) Ltd direct
27 Jan - 01 Feb Porter Airlines (Canada) Ltd direct
09 Jan - 15 Jan Porter Airlines (Canada) Ltd direct
11 Jan - 15 Jan Porter Airlines (Canada) Ltd direct
06 Jan - 22 Jan Porter Airlines (Canada) Ltd direct
06 Jan - 15 Jan Porter Airlines (Canada) Ltd direct
06 Jan - 08 Jan Porter Airlines (Canada) Ltd direct

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

Skyscanner

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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