$104 Cheap Porter Airlines flights Montreal (YUL) to Chicago (MDW)

Grab affordable round-trip Porter Airlines flights from $155 from YUL to MDW by sorting your results from "Price (lowest to highest)" on Expedia. Or search for deals from $104 for a one-way trip.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Snagging the best Porter Airlines deals from YUL to MDW often comes down to timing. You can save 17% on international flights when you book 18 to 29 days before takeoff instead of four to five months ahead. Better yet, you can pocket 17% on average by buying your fare on a Sunday rather than a Friday, which is usually the most expensive day to book.* It's smart to kick off your flight search about one month before you plan to travel.*Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.

To find the earliest departures from YUL to MDW with Porter Airlines, filter your search by "Early Morning" and "Morning." Booking an early flight usually means you're less likely to experience cancellations.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.

Offering an excellent in-flight experience, Porter Airlines is a popular choice for many passengers flying from YUL to MDW. Plus, as a VIPorter and One Key™ member booking through Expedia, you could earn OneKeyCash™* on eligible flights on top of your airline miles.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.