$167 Cheap Flights from Montreal (YUL) to Chicago (MDW)

View $167 flight on Sun, Nov 16, 2025Opens in a new window

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

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Cheap Flights from Montreal to Chicago (YUL-MDW)

Prices were available within the past 7 days and start at $167 for one-way flights and $270 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Sun, Nov 16 - Mon, Nov 24
YUL
Montreal
MDW
Chicago
$270 Roundtrip, found 3 days ago
$270
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Sun, Nov 16 from Montreal to Chicago, returning Mon, Nov 24, priced at $270 found 3 days ago
Porter Airlines
Tue, Oct 14 - Sun, Oct 19
YUL
Montreal
MDW
Chicago
$278 Roundtrip, found 2 days ago
$278
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Tue, Oct 14 from Montreal to Chicago, returning Sun, Oct 19, priced at $278 found 2 days ago
Porter Airlines
Fri, Nov 7 - Sun, Nov 9
YUL
Montreal
MDW
Chicago
$279 Roundtrip, found 1 day ago
$279
Roundtrip
found 1 day ago
Select Porter Airlines flight, departing Fri, Nov 7 from Montreal to Chicago, returning Sun, Nov 9, priced at $279 found 1 day ago
Porter Airlines
Fri, Dec 5 - Mon, Dec 8
YUL
Montreal
MDW
Chicago
$284 Roundtrip, found 3 days ago
$284
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Fri, Dec 5 from Montreal to Chicago, returning Mon, Dec 8, priced at $284 found 3 days ago
Delta
Sat, Dec 6 - Sun, Dec 7
YUL
Montreal
MDW
Chicago
$286 Roundtrip, found 5 hours ago
$286
Roundtrip
found 5 hours ago
Select Delta flight, departing Sat, Dec 6 from Montreal to Chicago, returning Sun, Dec 7, priced at $286 found 5 hours ago
Delta
Wed, Nov 26 - Sat, Nov 29
YUL
Montreal
MDW
Chicago
$293 Roundtrip, found 2 days ago
$293
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Nov 26 from Montreal to Chicago, returning Sat, Nov 29, priced at $293 found 2 days ago
Porter Airlines
Tue, Oct 14 - Sat, Nov 1
YUL
Montreal
MDW
Chicago
$294 Roundtrip, found 15 hours ago
$294
Roundtrip
found 15 hours ago
Select Porter Airlines flight, departing Tue, Oct 14 from Montreal to Chicago, returning Sat, Nov 1, priced at $294 found 15 hours ago
Porter Airlines
Mon, Oct 27 - Fri, Oct 31
YUL
Montreal
MDW
Chicago
$303 Roundtrip, found 5 hours ago
$303
Roundtrip
found 5 hours ago
Select Porter Airlines flight, departing Mon, Oct 27 from Montreal to Chicago, returning Fri, Oct 31, priced at $303 found 5 hours ago
Delta
Sun, Nov 16 - Mon, Nov 24
YUL
Montreal
MDW
Chicago
$306 Roundtrip, found 3 days ago
$306
Roundtrip
found 3 days ago
Select Delta flight, departing Sun, Nov 16 from Montreal to Chicago, returning Mon, Nov 24, priced at $306 found 3 days ago
WestJet
Sat, Nov 22 - Fri, Nov 28
YUL
Montreal
MDW
Chicago
$361 Roundtrip, found 2 days ago
$361
Roundtrip
found 2 days ago
Select WestJet flight, departing Sat, Nov 22 from Montreal to Chicago, returning Fri, Nov 28, priced at $361 found 2 days ago

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

November is typically the cheapest month to fly

From $163 - $414 per traveler.

Frequently asked questions

How much does a flight from Pierre Elliott Trudeau Intl. Airport (YUL) to Midway Intl. Airport (MDW) cost?
Secure a cheap one-way flight from $167 or cheap return flight from $270 from Pierre Elliott Trudeau Intl. Airport (YUL) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Pierre Elliott Trudeau Intl. Airport (YUL) to Midway Intl. Airport (MDW)?
November is the least expensive month to fly from YUL to MDW. Traveling outside of peak seasons is often the key to scoring lower fares.
What is the cheapest airline that flies from Pierre Elliott Trudeau Intl. Airport (YUL) to Midway Intl. Airport (MDW)?
To find the cheapest airline that'll fly you from YUL to MDW, use Expedia's filter tool. Customize your search based on what's important to you, such as preferred carriers and ideal departure window. You can then sort your results by "Price (lowest to highest)" to see the cheapest fares upfront.
How many flights per day from Pierre Elliott Trudeau Intl. Airport (YUL) to Midway Intl. Airport (MDW)?
You'll need to catch a flight with a layover when traveling from Pierre Elliott Trudeau Intl. Airport (YUL) to Midway Intl. Airport (MDW). Direct flights don't operate daily on this route. However, simply filter your search to include one or more stops to find an option that works for you.
What day of the week has the most flights from YUL to MDW?
You'll usually find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can change from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Pierre Elliott Trudeau Intl. Airport (YUL) to Midway Intl. Airport (MDW)?
To arrive at Midway Intl. Airport (MDW) without delays, pick a flight that leaves from Pierre Elliott Trudeau Intl. Airport (YUL) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this time.**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.
What airports do you fly into for Chicago from Pierre Elliott Trudeau Intl. Airport (YUL)?
If you're taking a direct flight from Pierre Elliott Trudeau Intl. Airport (YUL) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can land at.
Is it cheaper to buy a plane ticket from Pierre Elliott Trudeau Intl. Airport (YUL) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from YUL to MDW are typically more expensive. For the lowest rates, start looking for flights well in advance. That being said, if you're flexible with your travel plans, it's possible to score a cheap ticket just before your departure.
Is it cheaper to book a YUL to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking a YUL to MDW flight and hotel package with Expedia could lead to significant savings. Better still, having everything in one easy place takes the hassle out of travel planning. Just secure your flights and choose from our wide range of stays, then tailor your trip with extras like car rentals and activities.
Can I cancel or change the date of my flight from Pierre Elliott Trudeau Intl. Airport (YUL) to Midway Intl. Airport (MDW)?
Usually, it's possible to reschedule or cancel your YUL to MDW flight. However, for bookings made more than 24 hours ago, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are allowed and whether any costs are involved. You'll also find more details on our Customer Service portal.

Travel information

Travel information

Origin airport
Pierre Elliott Trudeau Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Porter Airlines, WestJet
Roundtrip price
$270
Distance
743 mi

Book with confidence

Book with confidence

Montreal to Chicago Flights

The cheapest times to fly from Montreal to Chicago

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 Montreal to Chicago are during the month of November. You can find some of the cheapest flights from Montreal to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Montreal to Chicago

Sunday is one of the best days to book for cheap flights from Montreal to Chicago: 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 Montreal to Chicago

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 Montreal to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $167 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 Montreal to Chicago 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 Montreal to Chicago 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.

 

Montreal to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.