$59 Cheap Flights from Chicago (MDW) to Montreal (YUL)

View $59 flight on Fri, Jan 16, 2026Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Montreal–Trudeau Intl. Airport (YUL)

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Cheap Flights from Chicago to Montreal (MDW-YUL)

Prices were available within the past 7 days and start at $59 for one-way flights and $170 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Wed, Jan 14 - Mon, Jan 19
MDW
Chicago
YUL
Montreal
$170 Roundtrip, found 1 hour ago
$170
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Wed, Jan 14 from Chicago to Montreal, returning Mon, Jan 19, priced at $170 found 1 hour ago
Porter Airlines
Fri, Jan 9 - Sat, Jan 24
MDW
Chicago
YUL
Montreal
$170 Roundtrip, found 2 days ago
$170
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Fri, Jan 9 from Chicago to Montreal, returning Sat, Jan 24, priced at $170 found 2 days ago
Porter Airlines
Fri, Mar 20 - Tue, Mar 24
MDW
Chicago
YUL
Montreal
$190 Roundtrip, found 1 day ago
$190
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Fri, Mar 20 from Chicago to Montreal, returning Tue, Mar 24, priced at $190 found 1 day ago
Porter Airlines
Wed, Feb 11 - Sun, Feb 15
MDW
Chicago
YUL
Montreal
$190 Roundtrip, found 2 days ago
$190
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Wed, Feb 11 from Chicago to Montreal, returning Sun, Feb 15, priced at $190 found 2 days ago
Porter Airlines
Mon, Mar 16 - Wed, Mar 18
MDW
Chicago
YUL
Montreal
$193 Roundtrip, found 11 hours ago
$193
Roundtrip
found 11 hours ago
Select Porter Airlines flight, departing Mon, Mar 16 from Chicago to Montreal, returning Wed, Mar 18, priced at $193 found 11 hours ago
Delta
Wed, Jun 3 - Sun, Jun 7
MDW
Chicago
YUL
Montreal
$214 Roundtrip, found 2 days ago
$214
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jun 3 from Chicago to Montreal, returning Sun, Jun 7, priced at $214 found 2 days ago
Delta
Wed, Jun 3 - Sun, Jun 7
MDW
Chicago
YUL
Montreal
$215 Roundtrip, found 2 days ago
$215
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Jun 3 from Chicago to Montreal, returning Sun, Jun 7, priced at $215 found 2 days ago
Porter Airlines
Wed, May 27 - Mon, Jun 1
MDW
Chicago
YUL
Montreal
$217 Roundtrip, found 2 hours ago
$217
Roundtrip
found 2 hours ago
Select Porter Airlines flight, departing Wed, May 27 from Chicago to Montreal, returning Mon, Jun 1, priced at $217 found 2 hours ago
Porter Airlines
Fri, Mar 20 - Tue, Mar 24
MDW
Chicago
YUL
Montreal
$228 Roundtrip, found 1 day ago
$228
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Fri, Mar 20 from Chicago to Montreal, returning Tue, Mar 24, priced at $228 found 1 day ago
WestJet
Thu, Dec 11 - Sun, Dec 14
MDW
Chicago
YUL
Montreal
$443 Roundtrip, just found
$443
Roundtrip
just found
Select WestJet flight, departing Thu, Dec 11 from Chicago to Montreal, returning Sun, Dec 14, priced at $443 just found

Find the cheapest month to fly from Chicago (MDW) to Montreal (YUL)

November is typically the cheapest month to fly

From $172 - $588 per traveler.

Alternative airports near Montreal

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Pierre Elliott Trudeau Intl. YUL. Cheapest and Closest option available. Average driving time to city center is 17 minutes. Flights from $553
YUL
Pierre Elliott Trudeau Intl.
CheapestClosest
Average driving time to city center17 min
Flights from $553

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Pierre Elliott Trudeau Intl. Airport (YUL) cost?
Secure a cheap one-way flight from $59 or cheap return flight from $170 from Midway Intl. Airport (MDW) to Pierre Elliott Trudeau Intl. Airport (YUL) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Pierre Elliott Trudeau Intl. Airport (YUL)?
January is the most affordable month to fly from MDW to YUL. Timing your trip outside of the busy season is often the key to scoring lower fares.
Which airlines fly direct from Midway Intl. Airport (MDW) to Pierre Elliott Trudeau Intl. Airport (YUL)?
You can't take a direct flight from Chicago, IL (MDW-Midway Intl.) to Pierre Elliott Trudeau Intl. Airport (YUL). However, you can easily travel to Montreal without any layovers by leaving from O'Hare Intl. Airport (ORD).
What is the cheapest airline that flies from Midway Intl. Airport (MDW) to Pierre Elliott Trudeau Intl. Airport (YUL)?
To find the cheapest airline that'll fly you from MDW to YUL, use Expedia's filter tool. Tailor your search based on your travel needs, such as preferred carriers and flight duration. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Midway Intl. Airport (MDW) to Pierre Elliott Trudeau Intl. Airport (YUL)?
There aren't any daily direct flights available from Midway Intl. Airport (MDW) to Pierre Elliott Trudeau Intl. Airport (YUL). But you can book flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be cruising above the clouds in no time at all.
What day of the week has the most flights from MDW to YUL?
Friday is typically the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can change depending on various factors, such as the airline and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Pierre Elliott Trudeau Intl. Airport (YUL)?
Select a flight from Midway Intl. Airport (MDW) to Pierre Elliott Trudeau Intl. Airport (YUL) that takes off before 3 PM to reduce the risk of cancellations. Departures after this hour have a 22% higher chance of being canceled, on average.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Pierre Elliott Trudeau Intl. Airport (YUL) last-minute?
Last-minute bookings from MDW to YUL are usually more expensive. For the lowest rates, start looking for flights ahead of time. That being said, if you're flexible with your travel dates, you may find a cheap fare right before your journey.
Is it cheaper to book a MDW to YUL flight and hotel package?
Booking a MDW to YUL flight and hotel package is generally cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Pick from our wide range of stays and then add activities, flights and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Pierre Elliott Trudeau Intl. Airport (YUL)?
Typically, it's possible to cancel or reschedule your MDW to YUL flight. However, if the booking was made more than 24 hours ago, additional fees may apply. Refer to your airline's policies in your itinerary to see what changes are possible and whether any costs are involved. You'll also find more details on our Customer Service portal.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Pierre Elliott Trudeau Intl.
Airlines serving
Delta, Porter Airlines, WestJet
Roundtrip price
$169
Distance
743 mi

Book with confidence

Book with confidence

Chicago to Montreal Flights

The cheapest times to fly from Chicago to Montreal

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Montreal are during the month of January. You can find some of the cheapest flights from Chicago to Montreal with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Montreal

Sunday is one of the best days to book for cheap flights from Chicago to Montreal: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Montreal

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Montreal in 2025. You can also book with separate airlines for your outbound and return journeys, from $59 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Montreal flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Montreal airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Chicago to Montreal Flights

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