Cheapest return flights from Toronto to Chicago in January from $171

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

Return flights

15 Jan - 27 Jan Porter Airlines (Canada) Ltd direct
15 Jan - 02 Feb Porter Airlines (Canada) Ltd direct
06 Jan - 13 Jan Porter Airlines (Canada) Ltd direct
05 Jan - 12 Jan Porter Airlines (Canada) Ltd direct
26 Jan - 27 Jan Porter Airlines (Canada) Ltd direct
05 Jan - 06 Jan Porter Airlines (Canada) Ltd direct
16 Jan - 27 Jan Porter Airlines (Canada) Ltd direct
26 Jan - 02 Feb Porter Airlines (Canada) Ltd direct
16 Jan - 02 Feb Porter Airlines (Canada) Ltd direct
05 Jan - 05 Jan Porter Airlines (Canada) Ltd direct
26 Jan - 09 Feb Porter Airlines (Canada) Ltd direct
06 Jan - 08 Jan Porter Airlines (Canada) Ltd direct
30 Jan - 01 Feb Porter Airlines (Canada) Ltd direct
05 Jan - 13 Jan Porter Airlines (Canada) Ltd direct
02 Jan - 06 Jan Porter Airlines (Canada) Ltd direct
18 Jan - 02 Feb Porter Airlines (Canada) Ltd direct
18 Jan - 06 Feb Porter Airlines (Canada) Ltd direct
13 Jan - 02 Feb Porter Airlines (Canada) Ltd direct
26 Jan - 15 Feb Porter Airlines (Canada) Ltd direct
26 Jan - 13 Feb Porter Airlines (Canada) Ltd direct

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

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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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