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

One-Way flights

24 Nov	Porter Airlines (Canada) Ltd
19 Nov	Porter Airlines (Canada) Ltd
01 Nov	Porter Airlines (Canada) Ltd
03 Nov	Porter Airlines (Canada) Ltd
05 Nov	Porter Airlines (Canada) Ltd
02 Nov	Porter Airlines (Canada) Ltd
04 Nov	Porter Airlines (Canada) Ltd
06 Nov	Porter Airlines (Canada) Ltd
07 Nov	Porter Airlines (Canada) Ltd
08 Nov	Porter Airlines (Canada) Ltd

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

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

Cheapest one-way flights from Montreal to Chicago in November from 95€

One-Way flights