HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$131+ 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 10/16. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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.

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 September 11, 2025.

Round-trip from

$209
(Kiwi.com)

One-way from

$131
(SmartFares)

Popular in

October

Cheapest in

September

Average price

$155
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, 3% potential price rise
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Sun 11/96:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Tue 11/1111:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Deal found 9/8$209
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/171:10 pmYUL - MDW
1 stop4h 14mPorter Airlines
Mon 10/205:20 pmMDW - YUL
1 stop3h 55mPorter Airlines
Deal found 9/9$210
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2111:25 amYUL - MDW
1 stop4h 55mPorter Airlines
Fri 11/2811:00 amMDW - YUL
1 stop5h 45mPorter Airlines
Deal found 9/10$211
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/71:10 pmYUL - MDW
1 stop4h 14mPorter Airlines
Wed 10/159:35 amMDW - YUL
1 stop5h 25mPorter Airlines
Deal found 9/9$214
This Trip.com deal was found by Cheapflights users on 9/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/710:45 amYUL - MDW
1 stop6h 39mPorter Airlines
Fri 10/245:20 pmMDW - YUL
1 stop3h 55mPorter Airlines
Deal found 9/9$215
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2011:25 amYUL - MDW
1 stop4h 55mPorter Airlines
Thu 11/274:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Deal found 9/10$216
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/810:45 amYUL - MDW
1 stop6h 39mPorter Airlines
Sun 10/125:20 pmMDW - YUL
1 stop3h 55mPorter Airlines
Deal found 9/10$218
This SmartFares deal was found by Cheapflights users on 9/8. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/1611:25 amYUL - MDW
1 stop4h 55mPorter Airlines
Tue 11/1811:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Deal found 9/8$221
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/196:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Tue 12/911:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Deal found 9/9$223

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 September 11, 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

Thu 11/20

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Sun 11/23

11:00 am-4:30 pm

1 stop4h 30m

$209

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 10/2

10:45 am-4:24 pm

1 stop6h 39m

Chicago Midway

Mon 10/6

5:20 pm-10:15 pm

1 stop3h 55m

$215

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 11/21

11:25 am-3:20 pm

1 stop4h 55m

Chicago Midway

Mon 11/24

11:00 am-4:30 pm

1 stop4h 30m

$227

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/17

10:45 am-4:24 pm

1 stop6h 39m

Chicago Midway

Mon 10/20

5:20 pm-10:15 pm

1 stop3h 55m

$237

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 10/8

1:10 pm-4:24 pm

1 stop4h 14m

Chicago Midway

Thu 10/9

9:35 am-4:00 pm

1 stop5h 25m

$238

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/17

10:45 am-4:24 pm

1 stop6h 39m

Chicago Midway

Tue 10/21

5:20 pm-10:15 pm

1 stop3h 55m

$239

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/17

1:10 pm-4:24 pm

1 stop4h 14m

Chicago Midway

Wed 10/22

5:20 pm-10:15 pm

1 stop3h 55m

$239

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 10/15

1:10 pm-4:24 pm

1 stop4h 14m

Chicago Midway

Sun 10/19

5:20 pm-10:15 pm

1 stop3h 55m

$239

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/31

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Sun 11/2

11:00 am-6:45 pm

1 stop6h 45m

$240

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 11/20

6:45 am-10:05 am

1 stop4h 20m

Chicago Midway

Thu 11/27

11:00 am-4:30 pm

1 stop4h 30m

$241

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 22 results
1
2
3

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, April is the cheapest month in which you can book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport (average of $160). Flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 September 11, 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
7.9
Good
363 reviews

Entertainment

7.0

Boarding

8.1

Comfort

7.9

Crew

8.6

Overall

7.9

Food

7.6

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
7.9
Good
363 reviews
Porter Airlines
7.9
Good
363 reviews

Entertainment

7.0

Boarding

8.1

Comfort

7.9

Crew

8.6

Overall

7.9

Food

7.6

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 4h 20m. Porter Airlines provides one of the quickest options available for as low as $209. The distance between Montreal Pierre Elliott Trudeau Intl Airport and Chicago Midway Airport is about 743 mi.

  • 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 27% 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, April is the cheapest month in which you can book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport (average of $160). Flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Benton Harbor
Porter
Chesterton

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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$226Average$325FlexibilityNo 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.