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$170+ Cheap flights from Pierre Elliott Trudeau Intl (YUL) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/31. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — MDW
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap flight deals from Pierre Elliott Trudeau Intl to Midway

Cheapest flights from Pierre Elliott Trudeau Intl to Midway
Explore the most affordable flight options available from Pierre Elliott Trudeau Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 12, 2025.

This FlightHub deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/276:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Mon 2/2311:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Deal found 12/11$238
This Trip.com deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Mon 1/54:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Deal found 12/10$313
This FlightHub deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Tue 1/611:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Deal found 12/11$326
This FlightHub deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Sat 1/311:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Deal found 12/11$328
This Flightnetwork deal was found by Cheapflights users on 12/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Sun 1/1111:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Deal found 12/9$348
This FlightHub deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/286:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Tue 12/304:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Deal found 12/10$367
This FlightHub deal was found by Cheapflights users on 12/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Mon 1/54:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Deal found 12/11$368
This Trip.com deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2510:15 amYUL - MDW
1 stop6h 05mPorter Airlines
Sun 12/2811:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Deal found 12/10$373
This Trip.com deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1911:25 amYUL - MDW
1 stop4h 55mPorter Airlines
Fri 1/211:00 amMDW - YUL
1 stop6h 45mPorter Airlines
Deal found 12/10$375
This FlightHub deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2611:25 amYUL - MDW
1 stop4h 55mPorter Airlines
Sun 12/2811:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Deal found 12/10$386
This Mytrip deal was found by Cheapflights users on 12/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2510:15 amYUL - MDW
1 stop6h 05mPorter Airlines
Mon 12/2911:00 amMDW - YUL
1 stop6h 45mPorter Airlines
Deal found 12/10$389

Find flight deals from Pierre Elliott Trudeau Intl to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Pierre Elliott Trudeau Intl (YUL) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$188
(Porter Airlines)

One-way from

$170
(FlightHub)

Popular in

October

Cheapest in

September

Average price

$327
Provider with most accurate pricing for Montreal Pierre Elliott Trudeau Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Montreal Pierre Elliott Trudeau Intl-Chicago Midway flights.
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From Montreal Pierre Elliott Trudeau Intl to Chicago Midway
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One-way flight from Montreal Pierre Elliott Trudeau Intl to Chicago Midway
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Highest demand for flights based on searches. 13% potential increase in price ($52 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Pierre Elliott Trudeau Intl to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
Use the filters below to find and compare flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport that are best for you.

Fly from

Pierre Elliott Trudeau Intl

Fly to

Midway

Route

Depart

Return

Price

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 2/14

8:55 am-11:50 am

1 stop3h 55m

Chicago Midway

Tue 2/17

11:00 am-6:45 pm

1 stop6h 45m

$188

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 2/17

7:00 am-11:59 am

1 stop5h 59m

Chicago Midway

Wed 2/18

1:28 pm-11:10 pm

1 stop8h 42m

$215

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 3/14

8:55 am-11:50 am

1 stop3h 55m

Chicago Midway

Tue 3/17

11:00 am-6:45 pm

1 stop6h 45m

$268

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 2/17

6:00 am-12:46 pm

1 stop7h 46m

Chicago Midway

Thu 2/19

6:00 am-4:53 pm

1 stop9h 53m

$273

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 1/5

6:45 am-10:10 am

1 stop4h 25m

Chicago Midway

Thu 1/8

11:05 am-5:45 pm

1 stop5h 40m

$290

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 3/6

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Mon 3/9

11:00 am-5:45 pm

1 stop5h 45m

$296

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 4/24

10:15 am-3:20 pm

1 stop6h 05m

Chicago Midway

Mon 4/27

4:15 pm-10:45 pm

1 stop5h 30m

$299

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 1/26

6:00 am-12:46 pm

1 stop7h 46m

Chicago Midway

Mon 2/2

1:26 pm-11:12 pm

1 stop8h 46m

$301

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 1/22

6:00 am-12:46 pm

1 stop7h 46m

Chicago Midway

Wed 1/28

1:26 pm-11:12 pm

1 stop8h 46m

$304

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 1/23

12:50 pm-10:22 pm

1 stop10h 32m

Chicago Midway

Mon 1/26

6:00 am-4:55 pm

1 stop9h 55m

$305

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 21 results
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Compare providers for flights from Pierre Elliott Trudeau Intl to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Pierre Elliott Trudeau Intl to Midway in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Montreal Pierre Elliott Trudeau Intl Airport-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Montreal Pierre Elliott Trudeau Intl Airport-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Montreal Pierre Elliott Trudeau Intl Airport-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Montreal Pierre Elliott Trudeau Intl Airport-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Montreal Pierre Elliott Trudeau Intl Airport-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Pierre Elliott Trudeau Intl to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Pierre Elliott Trudeau Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport

What is the cheapest month to book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

Currently, September is the cheapest month in which you can book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport (average of $131). Flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport in January is currently the most expensive (average of $306). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated December 12, 2025.
Get a feel of what it's like to fly with Porter Airlines from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
397 reviews

Crew

8.6

Food

7.6

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
8.0
Very good
397 reviews
Porter Airlines
8.0
Very good
397 reviews

Crew

8.6

Food

7.6

Comfort

8.0

Entertainment

7.0

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

Related info for your journey

Find useful and relevant information for your journey from Pierre Elliott Trudeau Intl to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

    A quick flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport can take about 3h 55m. Porter Airlines provides one of the quickest options available for as low as $188. The distance between Montreal Pierre Elliott Trudeau Intl Airport and Chicago Midway Airport is about 743 mi. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport round-trip?

    Our cheapest airline available from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport is Porter Airlines. Our recent data shows that you can find tickets from as low as $217 on this airline. You may be able to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport for 35% less than the average price by searching for this airline.

  • Can I find deals for flights from Pierre Elliott Trudeau Intl to Midway that include hotel bookings?

    Yes. In addition to deals on Pierre Elliott Trudeau Intl to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pierre Elliott Trudeau Intl to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Pierre Elliott Trudeau Intl to Midway.

  • Can I find deals for business class flights from Pierre Elliott Trudeau Intl to Midway?

    Yes. Cheapflights offers flight deals from Pierre Elliott Trudeau Intl to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

    Currently, September is the cheapest month in which you can book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport (average of $131). Flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport in January is currently the most expensive (average of $306). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Alternative routes for Pierre Elliott Trudeau Intl to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Pierre Elliott Trudeau Intl to O'Hare Intl flights

Top airline flying from Pierre Elliott Trudeau Intl to Midway

Discover the top airline that operate flights from Pierre Elliott Trudeau Intl to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$217Average$300FlexibilityNo cancel feeOn-time52%

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