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CA $250 Cheap Flights from Montreal (YUL) to Chicago (MDW)

View CA $250 flight on Wed, Oct 14, 2026Opens in a new window

Popular airlines from Trudeau International Airport (YUL) to Chicago Midway Airport (MDW)

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Cheap flights from Montreal (YUL) to Chicago (MDW)

Prices were available within the past 7 days and start at CA $250 for one-way flights and CA $417 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Sun, Nov 1 - Sat, Nov 21
YUL
Montreal
MDW
Chicago
CA $417 Roundtrip, found 9 hours ago
CA $417
Roundtrip
found 9 hours ago
Select Delta flight, departing Sun, Nov 1 from Montreal to Chicago, returning Sat, Nov 21, priced at CA $417 found 9 hours ago
Delta
Wed, Oct 21 - Wed, Oct 28
YUL
Montreal
MDW
Chicago
CA $417 Roundtrip, found 7 hours ago
CA $417
Roundtrip
found 7 hours ago
Select Delta flight, departing Wed, Oct 21 from Montreal to Chicago, returning Wed, Oct 28, priced at CA $417 found 7 hours ago
Delta
Sat, Sep 19 - Sat, Sep 26
YUL
Montreal
MDW
Chicago
CA $423 Roundtrip, found 7 hours ago
CA $423
Roundtrip
found 7 hours ago
Select Delta flight, departing Sat, Sep 19 from Montreal to Chicago, returning Sat, Sep 26, priced at CA $423 found 7 hours ago
Porter Airlines
Fri, Sep 25 - Sun, Sep 27
YUL
Montreal
MDW
Chicago
CA $425 Roundtrip, found 7 hours ago
CA $425
Roundtrip
found 7 hours ago
Select Porter Airlines flight, departing Fri, Sep 25 from Montreal to Chicago, returning Sun, Sep 27, priced at CA $425 found 7 hours ago
Porter Airlines
Sat, Sep 26 - Tue, Sep 29
YUL
Montreal
MDW
Chicago
CA $435 Roundtrip, found 6 hours ago
CA $435
Roundtrip
found 6 hours ago
Select Porter Airlines flight, departing Sat, Sep 26 from Montreal to Chicago, returning Tue, Sep 29, priced at CA $435 found 6 hours ago
Delta
Sun, Feb 21 - Sun, Feb 28
YUL
Montreal
MDW
Chicago
CA $440 Roundtrip, found 7 hours ago
CA $440
Roundtrip
found 7 hours ago
Select Delta flight, departing Sun, Feb 21 from Montreal to Chicago, returning Sun, Feb 28, priced at CA $440 found 7 hours ago
Delta
Tue, Oct 20 - Tue, Oct 27
YUL
Montreal
MDW
Chicago
CA $443 Roundtrip, found 7 hours ago
CA $443
Roundtrip
found 7 hours ago
Select Delta flight, departing Tue, Oct 20 from Montreal to Chicago, returning Tue, Oct 27, priced at CA $443 found 7 hours ago
Porter Airlines
Sat, Oct 17 - Wed, Oct 21
YUL
Montreal
MDW
Chicago
CA $447 Roundtrip, found 9 hours ago
CA $447
Roundtrip
found 9 hours ago
Select Porter Airlines flight, departing Sat, Oct 17 from Montreal to Chicago, returning Wed, Oct 21, priced at CA $447 found 9 hours ago
Porter Airlines
Fri, Sep 25 - Sun, Sep 27
YUL
Montreal
MDW
Chicago
CA $448 Roundtrip, found 7 hours ago
CA $448
Roundtrip
found 7 hours ago
Select Porter Airlines flight, departing Fri, Sep 25 from Montreal to Chicago, returning Sun, Sep 27, priced at CA $448 found 7 hours ago
Delta
Sat, Sep 19 - Thu, Oct 8
YUL
Montreal
MDW
Chicago
CA $450 Roundtrip, found 10 hours ago
CA $450
Roundtrip
found 10 hours ago
Select Delta flight, departing Sat, Sep 19 from Montreal to Chicago, returning Thu, Oct 8, priced at CA $450 found 10 hours ago

Alternative airports near Chicago

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

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from CA $441
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from CA $441

Frequently asked questions

How much does a flight from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find cheap one-way flights from CA $250 and cheap return flights from CA $417 YUL to MDW with Expedia. Return flights often range between CA$497 and CA$3614. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see the cheapest fares first, and use the Price Tracking tool to receive alerts when YUL to MDW ticket fares go up or down.
What is the cheapest month to fly from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest months to fly from YUL to MDW are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.
Which airlines fly direct from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.)?
Enter YUL to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.)?
Porter Airlines is one of the cheapest airlines offering connecting return flights from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.), with tickets starting from around CA$293 for flights that can be booked for departure within the next year. These prices are per adult, for economy/coach class. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
How do I find cheap flights from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.
What is the best time to fly from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.)?
The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.
How many flights per day from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.)?
There are approximately 11 connecting flights per day from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.). Some common connection points include Liberty Intl. (EWR), Pearson Intl. (YYZ), and Detroit Metropolitan Wayne County (DTW).
What is the earliest flight from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.) typically departs around 6:00 AM local time. This flight is operated by Delta. This is a seasonal service, active in June, July, August, and September. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.
What day of the week has the most flights from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.)?
You'll typically find the most flights from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.) on a Saturday, with around 21 flights available. This gives you a good selection of options for your travel plans. Major airlines on this route include Delta, Air Canada, and United. Flight schedules are fairly consistent throughout the week, with Saturdays having only slightly more options than other days.
What are the most popular departure times for flights from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.) are in the early morning, from 6am to 9am. Many major carriers, including Delta, WestJet and Porter Airlines, offer flights during this window. Many travellers prefer these times because it allows for an early start to their day at their destination.
How long does it take to fly from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.)?
There are no nonstop flights from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.). For flights with one stop, you can expect the journey to take around 6 hours. If you opt for flights with two or more stops, the travel time typically increases to about 12 hours 48 minutes. The distance between these two airports is approximately 1,196 kilometres. Keep in mind that actual flight times can vary due to factors like layover duration, routing, and weather conditions.
Can you fly business or first class from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.)?
You can fly business class or first class between YUL and MDW. First class cabins are available on Delta.
How do I earn miles on a Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.
What airports do you fly into for Chicago, IL (MDW) from Montreal, QC (YUL)?
If you're planning to travel to Chicago from Pierre Elliott Trudeau Intl. (YUL), you can fly directly into Midway Intl. (MDW). Some flights may connect through major hubs like Liberty Intl. (EWR), Washington Dulles Intl. (IAD), or Pearson Intl. (YYZ) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.
Is it cheaper to buy a plane ticket from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.
Is it cheaper to book a Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities 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 Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Montreal, QC (YUL-Pierre Elliott Trudeau Intl.) to Chicago, IL (MDW-Midway Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

Travel information

Origin airport
Pierre Elliott Trudeau Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Porter Airlines, WestJet
Roundtrip price
CA $416
Distance
1188 km

Book with confidence

Montreal to Chicago Flights

The easy way to book your flights from Montreal to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Montreal whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to Midway Intl., too.  

Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Montreal to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Pierre Elliott Trudeau Intl., YUL to Midway Intl., MDW 

Sort your search results by price to find great deals on your flight from Montreal to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Montreal currently is just CA $417 rising to CA $470.  

Here are more money-saving tips: 

  • Fly in November when flight prices are normally at their lowest 
  • Book about a month to 6 weeks before you travel for the best prices to Chicago  
  • Avoid peak season and weekends when flights can cost more
  • Early morning and late-night flights are sometimes cheaper, so try varying your travel times 
  • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! 

 

Reasons to choose Expedia for your flight to Chicago from Montreal 

Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

Montreal to Chicago Flights

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