Cheapest one-way flights from Toronto to Chicago in November from $88

AirHint found the following cheapest one-way flights from Toronto (YTZ) to Chicago (MDW) in November 2025 (see full year).

One-Way flights

12 Nov Porter Airlines (Canada) Ltd direct
01 Nov Porter Airlines (Canada) Ltd direct
04 Nov Porter Airlines (Canada) Ltd direct
11 Nov Porter Airlines (Canada) Ltd direct
13 Nov Porter Airlines (Canada) Ltd direct
25 Nov Porter Airlines (Canada) Ltd direct
18 Nov Porter Airlines (Canada) Ltd direct
08 Nov Porter Airlines (Canada) Ltd direct
29 Nov Porter Airlines (Canada) Ltd direct
27 Nov Porter Airlines (Canada) Ltd direct

Also check the deals for return flights from Toronto to Chicago in November.

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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