$134 Cheap Flights from Montreal (YUL) to Chicago (MDW)

View $134 flight on Wed, May 21, 2025Opens in a new window
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Cheap Flights from Montreal to Chicago (YUL-MDW)

Prices were available within the past 7 days and start at $134 for one-way flights and $215 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Thu, May 22 - Sun, May 25
YUL
Montreal
MDW
Chicago
$215 Roundtrip, found 4 hours ago
$215
Roundtrip
found 4 hours ago
Select Porter Airlines flight, departing Thu, May 22 from Montreal to Chicago, returning Sun, May 25, priced at $215 found 4 hours ago
Delta
Thu, Jul 24 - Mon, Jul 28
YUL
Montreal
MDW
Chicago
$230 Roundtrip, found 3 days ago
$230
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Jul 24 from Montreal to Chicago, returning Mon, Jul 28, priced at $230 found 3 days ago
Porter Airlines
Thu, May 8 - Sun, May 25
YUL
Montreal
MDW
Chicago
$235 Roundtrip, found 4 hours ago
$235
Roundtrip
found 4 hours ago
Select Porter Airlines flight, departing Thu, May 8 from Montreal to Chicago, returning Sun, May 25, priced at $235 found 4 hours ago
Porter Airlines
Fri, Jul 18 - Sun, Jul 20
YUL
Montreal
MDW
Chicago
$239 Roundtrip, found 3 days ago
$239
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Fri, Jul 18 from Montreal to Chicago, returning Sun, Jul 20, priced at $239 found 3 days ago
Delta
Sat, Jun 14 - Sun, Jun 15
YUL
Montreal
MDW
Chicago
$245 Roundtrip, found 3 days ago
$245
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Jun 14 from Montreal to Chicago, returning Sun, Jun 15, priced at $245 found 3 days ago
Delta
Thu, May 22 - Sun, May 25
YUL
Montreal
MDW
Chicago
$246 Roundtrip, found 4 hours ago
$246
Roundtrip
found 4 hours ago
Select Delta flight, departing Thu, May 22 from Montreal to Chicago, returning Sun, May 25, priced at $246 found 4 hours ago
Delta
Sat, May 10 - Tue, May 13
YUL
Montreal
MDW
Chicago
$250 Roundtrip, found 2 days ago
$250
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, May 10 from Montreal to Chicago, returning Tue, May 13, priced at $250 found 2 days ago
Delta
Sat, Jun 28 - Thu, Jul 17
YUL
Montreal
MDW
Chicago
$250 Roundtrip, found 1 day ago
$250
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Jun 28 from Montreal to Chicago, returning Thu, Jul 17, priced at $250 found 1 day ago
Porter Airlines
Sat, Dec 6 - Mon, Dec 8
YUL
Montreal
MDW
Chicago
$253 Roundtrip, found 4 days ago
$253
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Sat, Dec 6 from Montreal to Chicago, returning Mon, Dec 8, priced at $253 found 4 days ago
WestJet
Tue, Jun 10 - Tue, Jun 17
YUL
Montreal
MDW
Chicago
$333 Roundtrip, found 3 days ago
$333
Roundtrip
found 3 days ago
Select WestJet flight, departing Tue, Jun 10 from Montreal to Chicago, returning Tue, Jun 17, priced at $333 found 3 days ago
Flights from Montreal (YUL) to Chicago (MDW)
Origin airport
Pierre Elliott Trudeau Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Porter Airlines, WestJet
Roundtrip price
$215
Distance
743 mi

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 May. 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 $134 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.

Frequently asked questions

How much does a flight from Pierre Elliott Trudeau Intl. Airport (YUL) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from YUL to MDW 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 YUL to MDW?
The cheapest flights from YUL to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from YUL to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from YUL to MDW. Sort your results by “Price (lowest to highest)” to snap up a great deal.
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.

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*Available to One Key members.