Cheapest return flights from Toronto to Chicago in January from 253€

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

Return flights

11 Jan - 13 Feb Porter Airlines (Canada) Ltd direct
01 Jan - 02 Jan Porter Airlines (Canada) Ltd direct
01 Jan - 04 Jan Porter Airlines (Canada) Ltd direct
01 Jan - 03 Jan Porter Airlines (Canada) Ltd direct
01 Jan - 01 Jan Porter Airlines (Canada) Ltd direct
04 Jan - 04 Jan Porter Airlines (Canada) Ltd direct
30 Jan - 30 Jan Porter Airlines (Canada) Ltd direct
30 Jan - 31 Jan Porter Airlines (Canada) Ltd direct
02 Jan - 03 Jan Porter Airlines (Canada) Ltd direct
02 Jan - 02 Jan Porter Airlines (Canada) Ltd direct
30 Jan - 12 Feb Porter Airlines (Canada) Ltd direct
30 Jan - 13 Feb Porter Airlines (Canada) Ltd direct
30 Jan - 15 Feb Porter Airlines (Canada) Ltd direct
30 Jan - 16 Feb Porter Airlines (Canada) Ltd direct
30 Jan - 18 Feb Porter Airlines (Canada) Ltd direct
30 Jan - 11 Feb Porter Airlines (Canada) Ltd direct
03 Jan - 04 Jan Porter Airlines (Canada) Ltd direct
30 Jan - 09 Feb 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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