HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$162+ 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 11/25. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — MDW
nov. 26 — dic. 31
mié. 11/26
mié. 12/3
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Pierre Elliott Trudeau Intl to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Find 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 octubre 27, 2025.

This Trip.com deal was found by Cheapflights users on 10/25. 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.
jue. 12/410:15 amYUL - MDW
1 stop6h 05mPorter Airlines
dom. 12/711:00 amMDW - YUL
1 stop5h 45mPorter Airlines
Deal found 10/25$263
This Trip.com deal was found by Cheapflights users on 10/26. 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.
mar. 12/96:45 amYUL - MDW
1 stop4h 20mPorter Airlines
vie. 12/1211:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Deal found 10/26$265
This Trip.com deal was found by Cheapflights users on 10/25. 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.
sáb. 11/228:55 amYUL - MDW
1 stop3h 55mPorter Airlines
sáb. 11/2912:45 pmMDW - YUL
1 stop5h 05mPorter Airlines
Deal found 10/25$272
This Trip.com deal was found by Cheapflights users on 10/25. 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.
lun. 11/246:45 amYUL - MDW
1 stop4h 20mPorter Airlines
sáb. 11/2912:45 pmMDW - YUL
1 stop5h 05mPorter Airlines
Deal found 10/25$276
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/228:55 amYUL - MDW
1 stop3h 55mPorter Airlines
lun. 11/244:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Deal found 10/26$280
This Kissandfly.com deal was found by Cheapflights users on 10/27. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/1111:25 amYUL - MDW
1 stop4h 55mPorter Airlines
jue. 12/1811:00 amMDW - YUL
1 stop5h 45mPorter Airlines
Deal found 10/27$281
This Kissandfly.com deal was found by Cheapflights users on 10/26. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/2010:15 amYUL - MDW
1 stop6h 05mPorter Airlines
lun. 11/2411:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Deal found 10/26$285
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/196:45 amYUL - MDW
1 stop4h 20mPorter Airlines
mar. 11/2511:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Deal found 10/26$286
This FlightHub deal was found by Cheapflights users on 10/26. 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.
vie. 11/2111:25 amYUL - MDW
1 stop4h 55mPorter Airlines
lun. 11/244:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Deal found 10/26$288

Cheap 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 octubre 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$263
(Trip.com)

One-way from

$162
(Kiwi.com)

Popular in

October

Cheapest in

September

Average price

$448
Provider with most accurate pricing for Montreal Pierre Elliott Trudeau Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Montreal Pierre Elliott Trudeau Intl-Chicago Midway flights.
Search Deals
From Montreal Pierre Elliott Trudeau Intl to Chicago Midway
Search Deals
One-way flight from Montreal Pierre Elliott Trudeau Intl to Chicago Midway
Search Deals
High demand for flights, 2% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 octubre 27, 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

jue. 12/4

10:15 am-3:20 pm

1 stop6h 05m

Chicago Midway

dom. 12/7

11:00 am-5:45 pm

1 stop5h 45m

$263

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

jue. 1/8

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

vie. 1/16

11:00 am-7:15 pm

1 stop7h 15m

$268

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

lun. 3/2

12:45 pm-9:46 pm

1 stop10h 01m

Chicago Midway

lun. 3/9

2:00 pm-11:39 pm

1 stop8h 39m

$275

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

jue. 12/11

11:25 am-3:20 pm

1 stop4h 55m

Chicago Midway

jue. 12/18

11:00 am-5:45 pm

1 stop5h 45m

$281

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

jue. 11/20

10:15 am-3:20 pm

1 stop6h 05m

Chicago Midway

lun. 11/24

11:00 am-4:30 pm

1 stop4h 30m

$285

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

vie. 11/21

11:25 am-3:20 pm

1 stop4h 55m

Chicago Midway

lun. 11/24

4:15 pm-10:45 pm

1 stop5h 30m

$285

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

dom. 11/23

12:50 pm-6:08 pm

1 stop6h 18m

Chicago Midway

mié. 11/26

9:34 am-3:55 pm

1 stop5h 21m

$302

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

mié. 11/26

6:26 pm-11:40 pm

1 stop6h 14m

Chicago Midway

lun. 12/1

5:34 pm-11:59 pm

1 stop5h 25m

$302

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

vie. 11/21

6:26 pm-11:40 pm

1 stop6h 14m

Chicago Midway

mar. 11/25

10:47 am-5:21 pm

1 stop5h 34m

$302

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

jue. 11/20

7:00 am-11:52 am

1 stop5h 52m

Chicago Midway

lun. 11/24

1:47 pm-11:42 pm

1 stop8h 55m

$302

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 22 results
1
2
3

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 October.
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 $300). 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 octubre 27, 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
384 reviews

Food

7.6

Comfort

8.0

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
8.0
Very good
384 reviews
Porter Airlines
8.0
Very good
384 reviews

Food

7.6

Comfort

8.0

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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 6h 05m. Porter Airlines provides one of the quickest options available for as low as $263. 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 $226 on this airline. You may be able to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport for 28% 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 $300). 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
Merrillville
Lansing
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 octubre 27, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$226Average$309FlexibilityNo cancel feeOn-time52%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.