$101 Cheap Flights from Chicago (MDW) to Montreal (YUL)

View $101 flight on Fri, Jul 25, 2025Opens in a new window
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Cheap Flights from Chicago to Montreal (MDW-YUL)

Prices were available within the past 7 days and start at $101 for one-way flights and $242 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, Jul 18 - Tue, Jul 22
MDW
Chicago
YUL
Montreal
$242 Roundtrip, found 12 hours ago
$242
Roundtrip
found 12 hours ago
Select Delta flight, departing Fri, Jul 18 from Chicago to Montreal, returning Tue, Jul 22, priced at $242 found 12 hours ago
Porter Airlines
Fri, Jun 20 - Sat, Jun 28
MDW
Chicago
YUL
Montreal
$246 Roundtrip, found 3 days ago
$246
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Fri, Jun 20 from Chicago to Montreal, returning Sat, Jun 28, priced at $246 found 3 days ago
Porter Airlines
Thu, May 22 - Sun, May 25
MDW
Chicago
YUL
Montreal
$248 Roundtrip, found 1 day ago
$248
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Thu, May 22 from Chicago to Montreal, returning Sun, May 25, priced at $248 found 1 day ago
Porter Airlines
Tue, May 20 - Tue, Jun 10
MDW
Chicago
YUL
Montreal
$254 Roundtrip, found 2 days ago
$254
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Tue, May 20 from Chicago to Montreal, returning Tue, Jun 10, priced at $254 found 2 days ago
Delta
Tue, May 13 - Sun, May 18
MDW
Chicago
YUL
Montreal
$268 Roundtrip, found 3 days ago
$268
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, May 13 from Chicago to Montreal, returning Sun, May 18, priced at $268 found 3 days ago
Delta
Fri, Jul 18 - Tue, Jul 22
MDW
Chicago
YUL
Montreal
$269 Roundtrip, found 12 hours ago
$269
Roundtrip
found 12 hours ago
Select Delta flight, departing Fri, Jul 18 from Chicago to Montreal, returning Tue, Jul 22, priced at $269 found 12 hours ago
Porter Airlines
Fri, Jun 20 - Sat, Jun 28
MDW
Chicago
YUL
Montreal
$270 Roundtrip, found 3 days ago
$270
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Fri, Jun 20 from Chicago to Montreal, returning Sat, Jun 28, priced at $270 found 3 days ago
Porter Airlines
Fri, Jun 20 - Sat, Jun 28
MDW
Chicago
YUL
Montreal
$274 Roundtrip, found 3 days ago
$274
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Fri, Jun 20 from Chicago to Montreal, returning Sat, Jun 28, priced at $274 found 3 days ago
Delta
Sat, Dec 6 - Tue, Dec 9
MDW
Chicago
YUL
Montreal
$275 Roundtrip, found 3 days ago
$275
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Dec 6 from Chicago to Montreal, returning Tue, Dec 9, priced at $275 found 3 days ago
WestJet
Tue, May 27 - Tue, Jun 3
MDW
Chicago
YUL
Montreal
$406 Roundtrip, found 4 hours ago
$406
Roundtrip
found 4 hours ago
Select WestJet flight, departing Tue, May 27 from Chicago to Montreal, returning Tue, Jun 3, priced at $406 found 4 hours ago

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Pierre Elliott Trudeau Intl. Airport (YUL) cost?
Discover the latest flight deals from MDW to YUL by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to YUL?
The cheapest flights from MDW to YUL are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
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 MDW to YUL?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from MDW to YUL. Sort your results by “Price (lowest to highest)” to snap up a great deal.
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.
*Available to One Key members.