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$102+ 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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — MDW
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
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 January 27, 2026.

This oojo deal was found by Cheapflights users on 1/27. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:30 am
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Mon 5/410:25 am
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 1/27$183
This FlightHub deal was found by Cheapflights users on 1/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:45 am
YUL
-
MDW
1 stop4h 20m
Porter Airlines
Mon 4/2011:00 am
MDW
-
YUL
1 stop4h 30m
Porter Airlines
Deal found 1/25$186
This FlightHub deal was found by Cheapflights users on 1/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/410:35 am
YUL
-
MDW
1 stop7h 15m
Porter Airlines
Sun 6/710:25 am
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 1/25$197
This FlightHub deal was found by Cheapflights users on 1/26. 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.
Fri 4/2411:25 am
YUL
-
MDW
1 stop4h 55m
Porter Airlines
Mon 4/2711:00 am
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 1/26$198
This FlightHub deal was found by Cheapflights users on 1/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2910:45 am
YUL
-
MDW
1 stop6h 39m
Porter Airlines
Mon 6/110:25 am
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 1/25$199
This FlightHub deal was found by Cheapflights users on 1/25. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/261:10 pm
YUL
-
MDW
1 stop4h 14m
Porter Airlines
Fri 5/2910:25 am
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 1/25$202
This Porter Airlines deal was found by Cheapflights users on 1/26. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/26:30 am
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Mon 6/810:25 am
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 1/26$205
This Porter Airlines deal was found by Cheapflights users on 1/26. 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 Porter Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/110:35 am
YUL
-
MDW
1 stop7h 15m
Porter Airlines
Sun 6/710:25 am
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 1/26$214
This Delta deal was found by Cheapflights users on 1/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:45 pm
YUL
-
MDW
1 stop10h 00m
Delta
Tue 6/26:00 am
MDW
-
YUL
1 stop10h 07m
Delta
Deal found 1/26$218

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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$183
(oojo)

One-way from

$102
(Trip.com)

Popular in

January

Cheapest in

September

Average price

$554
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. 9% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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 January 27, 2026.
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 6/4

6:30 am-9:40 am

1 stop4h 10m

Chicago Midway

Sun 6/7

10:25 am-5:15 pm

1 stop5h 50m

$186

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 6/5

10:35 am-4:50 pm

1 stop7h 15m

Chicago Midway

Mon 6/8

10:25 am-5:15 pm

1 stop5h 50m

$205

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 6/2

6:30 am-9:40 am

1 stop4h 10m

Chicago Midway

Thu 6/4

10:25 am-5:15 pm

1 stop5h 50m

$205

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 5/29

10:35 am-4:50 pm

1 stop7h 15m

Chicago Midway

Mon 6/1

10:25 am-5:15 pm

1 stop5h 50m

$205

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 5/28

6:30 am-9:40 am

1 stop4h 10m

Chicago Midway

Mon 6/1

10:25 am-5:15 pm

1 stop5h 50m

$205

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 6/3

12:25 pm-4:50 pm

1 stop5h 25m

Chicago Midway

Mon 6/8

10:25 am-5:15 pm

1 stop5h 50m

$205

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 6/1

12:25 pm-4:50 pm

1 stop5h 25m

Chicago Midway

Fri 6/5

10:25 am-5:15 pm

1 stop5h 50m

$205

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 6/1

10:35 am-4:50 pm

1 stop7h 15m

Chicago Midway

Sun 6/7

10:25 am-5:15 pm

1 stop5h 50m

$214

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 3/12

12:50 pm-5:54 pm

1 stop6h 04m

Chicago Midway

Mon 3/16

6:34 pm-11:13 pm

1 stop3h 39m

$218

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 3/22

6:00 am-12:29 pm

1 stop7h 29m

Chicago Midway

Wed 3/25

2:05 pm-11:40 pm

1 stop8h 35m

$218

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 22 results
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2
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  • Most accurate provider: When it comes to deals on Montreal Pierre Elliott Trudeau Intl Airport-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Montreal Pierre Elliott Trudeau Intl Airport-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 $490). 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 January 27, 2026.
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
412 reviews

Entertainment

6.9

Crew

8.6

Food

7.5

Overall

7.9

Comfort

7.9

Boarding

8.2

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
7.9
Good
412 reviews
Porter Airlines
7.9
Good
412 reviews

Entertainment

6.9

Crew

8.6

Food

7.5

Overall

7.9

Comfort

7.9

Boarding

8.2

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 4h 10m. Porter Airlines provides one of the quickest options available for as low as $186. 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 $217 on this airline. You may be able to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport for 38% 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 $490). 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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$217Average$300FlexibilityNo cancel feeOn-time52%

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