Cheapest one-way flights from Toronto to Chicago in November from $104

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

One-Way flights

27 Nov Porter Airlines (Canada) Ltd direct
28 Nov Porter Airlines (Canada) Ltd direct
21 Nov Porter Airlines (Canada) Ltd
23 Nov Porter Airlines (Canada) Ltd direct
22 Nov Porter Airlines (Canada) Ltd direct
24 Nov Porter Airlines (Canada) Ltd direct
19 Nov Porter Airlines (Canada) Ltd direct
30 Nov Porter Airlines (Canada) Ltd direct
15 Nov Porter Airlines (Canada) Ltd direct
29 Nov Porter Airlines (Canada) Ltd direct

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

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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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