Cheapest return flights from Toronto to Chicago in November from $143

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

Return flights

15 Nov - 19 Nov Porter Airlines (Canada) Ltd direct
05 Nov - 08 Nov Porter Airlines (Canada) Ltd direct
05 Nov - 06 Nov Porter Airlines (Canada) Ltd direct
05 Nov - 16 Nov Porter Airlines (Canada) Ltd direct
05 Nov - 22 Nov Porter Airlines (Canada) Ltd direct
05 Nov - 24 Nov Porter Airlines (Canada) Ltd direct
05 Nov - 14 Nov Porter Airlines (Canada) Ltd direct
05 Nov - 12 Nov Porter Airlines (Canada) Ltd direct
05 Nov - 09 Nov Porter Airlines (Canada) Ltd direct
04 Nov - 05 Nov Porter Airlines (Canada) Ltd direct
25 Nov - 07 Dec Porter Airlines (Canada) Ltd direct
18 Nov - 07 Dec Porter Airlines (Canada) Ltd direct
16 Nov - 07 Dec Porter Airlines (Canada) Ltd direct
11 Nov - 01 Dec Porter Airlines (Canada) Ltd direct
13 Nov - 01 Dec Porter Airlines (Canada) Ltd direct
25 Nov - 01 Dec Porter Airlines (Canada) Ltd direct
18 Nov - 01 Dec Porter Airlines (Canada) Ltd direct
16 Nov - 01 Dec Porter Airlines (Canada) Ltd direct
26 Nov - 07 Dec Porter Airlines (Canada) Ltd direct
15 Nov - 01 Dec Porter Airlines (Canada) Ltd direct

Also check the deals for one-way 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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