Cheapest return flights from Toronto to Chicago in November from $166

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

Return flights

11 Nov - 19 Nov Porter Airlines (Canada) Ltd direct
03 Nov - 08 Nov Porter Airlines (Canada) Ltd direct
07 Nov - 09 Nov Porter Airlines (Canada) Ltd direct
24 Nov - 26 Nov Porter Airlines (Canada) Ltd direct
14 Nov - 17 Nov Porter Airlines (Canada) Ltd direct
14 Nov - 16 Nov Porter Airlines (Canada) Ltd direct
20 Nov - 22 Nov Porter Airlines (Canada) Ltd direct
30 Nov - 03 Dec Porter Airlines (Canada) Ltd direct
11 Nov - 20 Nov Porter Airlines (Canada) Ltd direct
07 Nov - 22 Nov Porter Airlines (Canada) Ltd direct
03 Nov - 20 Nov Porter Airlines (Canada) Ltd direct
17 Nov - 03 Dec Porter Airlines (Canada) Ltd direct
24 Nov - 03 Dec Porter Airlines (Canada) Ltd direct
21 Nov - 03 Dec Porter Airlines (Canada) Ltd direct
16 Nov - 03 Dec Porter Airlines (Canada) Ltd direct
20 Nov - 03 Dec Porter Airlines (Canada) Ltd direct
14 Nov - 03 Dec Porter Airlines (Canada) Ltd direct
12 Nov - 03 Dec Porter Airlines (Canada) Ltd direct
13 Nov - 03 Dec Porter Airlines (Canada) Ltd direct
24 Nov - 10 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.

Book a cheap hotel in Chicago

Cheap car rent in Chicago

Feel free to contact us with any feedback or request another flight research.