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$90+ Cheap flights from Midway (MDW) to Montreal (YMQ)

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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YMQ
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
1 adult, Economy
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Cheap flight deals from Midway to Montreal

Cheapest flights from Midway to Montreal
Explore the most affordable flight options available from Midway to Montreal. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 4, 2025.

This FlightHub deal was found by Cheapflights users on 12/2. 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 12/3011:00 amMDW - YUL
1 stop5h 45mPorter Airlines
Mon 1/510:15 amYUL - MDW
1 stop6h 05mPorter Airlines
Deal found 12/2$312
This Trip.com deal was found by Cheapflights users on 12/3. 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 12/264:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Sun 12/286:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 12/3$318
This Trip.com deal was found by Cheapflights users on 12/3. 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.
Wed 12/2411:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Sat 12/276:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 12/3$321
This Trip.com deal was found by Cheapflights users on 12/1. 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 12/3011:00 amMDW - YUL
1 stop5h 45mPorter Airlines
Sun 1/46:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 12/1$325
This Trip.com deal was found by Cheapflights users on 12/2. 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.
Wed 12/2411:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Sun 12/286:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 12/2$330
This Trip.com deal was found by Cheapflights users on 12/2. 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 12/1911:00 amMDW - YUL
1 stop6h 45mPorter Airlines
Mon 12/226:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 12/2$335
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 12/186:12 amMDW - YUL
2 stops17h 18mMultiple Airlines
Mon 12/226:45 amYUL - MDW
1 stop4h 20mMultiple Airlines
Deal found 12/1$347
This FlightHub deal was found by Cheapflights users on 12/3. 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 12/264:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Tue 12/306:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 12/3$350
This Trip.com deal was found by Cheapflights users on 12/2. 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.
Mon 12/2911:00 amMDW - YUL
1 stop6h 45mPorter Airlines
Fri 1/26:45 amYUL - MDW
1 stop4h 25mPorter Airlines
Deal found 12/2$361
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/234:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Sun 12/286:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 12/3$366

Find flight deals from Midway to Montreal

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Montreal (YMQ). 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 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$217
(FlightHub)

One-way from

$90
(Mytrip)

Popular in

June

Cheapest in

September

Average price

$402
Provider with most accurate pricing for Chicago Midway-Montreal (YMQ) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Montreal (YMQ) flights.
Search Deals
From Chicago Midway to Montreal (YMQ)
Search Deals
One-way flight from Chicago Midway to Montreal (YMQ)
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Montreal 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 4, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Montreal that are best for you.

Fly from

Midway

Fly to

Montreal

Route

Depart

Return

Price

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 4/10

11:00 am-4:30 pm

1 stop4h 30m

Montreal Pierre Elliott Trudeau Intl

Sun 4/12

10:15 am-3:20 pm

1 stop6h 05m

$227

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sat 2/14

1:28 pm-11:10 pm

1 stop8h 42m

Montreal Pierre Elliott Trudeau Intl

Sat 2/21

6:00 am-12:46 pm

1 stop7h 46m

$236

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Wed 1/14

6:45 am-1:32 pm

1 stop5h 47m

Montreal Pierre Elliott Trudeau Intl

Sun 1/18

6:00 am-12:48 pm

1 stop7h 48m

$264

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 2/5

6:00 am-4:55 pm

1 stop9h 55m

Montreal Pierre Elliott Trudeau Intl

Mon 2/9

6:00 am-12:46 pm

1 stop7h 46m

$264

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 1/22

10:48 am-4:55 pm

1 stop5h 07m

Montreal Pierre Elliott Trudeau Intl

Sun 1/25

12:50 pm-10:22 pm

1 stop10h 32m

$264

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 2/27

1:28 pm-11:10 pm

1 stop8h 42m

Montreal Pierre Elliott Trudeau Intl

Sun 3/1

6:00 am-12:46 pm

1 stop7h 46m

$286

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 3/5

11:00 am-6:45 pm

1 stop6h 45m

Montreal Pierre Elliott Trudeau Intl

Sun 3/8

11:25 am-3:20 pm

1 stop4h 55m

$305

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 2/13

4:15 pm-10:45 pm

1 stop5h 30m

Montreal Pierre Elliott Trudeau Intl

Sun 2/15

11:25 am-3:20 pm

1 stop4h 55m

$307

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 3/27

11:00 am-4:30 pm

1 stop4h 30m

Montreal Pierre Elliott Trudeau Intl

Tue 3/31

6:45 am-10:05 am

1 stop4h 20m

$307

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 2/12

11:05 am-4:30 pm

1 stop4h 25m

Montreal Pierre Elliott Trudeau Intl

Sun 2/15

10:15 am-3:20 pm

1 stop6h 05m

$329

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

Showing 1-10 of 21 results
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Compare providers for flights from Midway to Montreal

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 Midway to Montreal in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
Trip.comPrice Accuracy2 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 Chicago Midway Airport-Montreal flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Montreal flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Montreal flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Montreal 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 Chicago Midway Airport-Montreal 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 Midway to Montreal

Have a flexible travel schedule? Discover the best time to fly to Montreal from Midway 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 Chicago Midway Airport to Montreal

How often are flights from Chicago to Montreal delayed?

About 31% of weekly flights between Chicago and Montreal have experienced delays in the past year, with the average delay time being 61 minutes.

What is the most punctual flight time for Chicago to Montreal flights?

Historically, flights departing in the morning are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Monday tends to have the lowest number of delays on this route, whereas Saturday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Chicago to Montreal flights?

Over the last year, Air Canada have had the lowest number of delays on this route, with just 50% of flights being delayed.

Reviews of airlines servicing Montreal

Get insights into the airlines that provide service to Montreal. 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 Montreal. Reviews last updated December 4, 2025.
Read reviews from past customers who have flown Porter Airlines from Chicago Midway Airport to Montreal. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
394 reviews

Food

7.6

Comfort

8.0

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.6

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
394 reviews
Porter Airlines
8.0
Very good
394 reviews

Food

7.6

Comfort

8.0

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.6

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 Midway to Montreal. 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 Chicago Midway Airport to Montreal?

    Departing from Chicago Midway Airport to Montreal will take you 4h 30m. The distance between Chicago Midway Airport and Montreal is about 743 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Porter Airlines, at $249, was found to be the cheapest airline from Chicago Midway Airport to Montreal..

  • Can I find deals for flights from Midway to Montreal that include hotel bookings?

    Yes. In addition to deals on Midway to Montreal flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Montreal?

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

  • Can I find deals for business class flights from Midway to Montreal?

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

See more FAQs

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.

Top airline flying from Midway to Montreal

Discover the top airline that operate flights from Midway to Montreal. 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 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$249Average$457FlexibilityNo cancel feeOn-time52%

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