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$137+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YMQ
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
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Cheap 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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$222
(Kiwi.com)

One-way from

$137
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$330
Provider with most accurate pricing for Chicago Midway-Montreal (YMQ) flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Montreal (YMQ) flights.
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From Chicago Midway to Montreal (YMQ)
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One-way flight from Chicago Midway to Montreal (YMQ)
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Highest demand for flights based on searches. 7% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 14, 2025.

This Trip.com deal was found by Cheapflights users on 10/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/174:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Fri 11/216:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 10/11$306
This Mytrip deal was found by Cheapflights users on 10/13. 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 11/204:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Fri 11/216:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 10/13$314
This Trip.com deal was found by Cheapflights users on 10/14. 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 11/1311:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Sun 11/166:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 10/14$321
This Trip.com deal was found by Cheapflights users on 10/13. 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 11/411:00 amMDW - YUL
1 stop5h 45mPorter Airlines
Wed 11/56:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 10/13$324
This Trip.com deal was found by Cheapflights users on 10/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/611:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Sun 11/96:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 10/11$325
This Mytrip deal was found by Cheapflights users on 10/12. 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.
Wed 11/2611:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Wed 12/36:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 10/12$329
This Mytrip deal was found by Cheapflights users on 10/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/911:00 amMDW - YUL
1 stop5h 45mPorter Airlines
Sun 11/166:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 10/11$333
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 12/114:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Sun 12/146:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 10/13$334
This Delta deal was found by Cheapflights users on 10/13. 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.
Wed 11/269:34 amMDW - YUL
1 stop5h 21mDelta
Tue 12/26:30 pmYUL - MDW
1 stop6h 19mDelta
Deal found 10/13$341

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 October 14, 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

Sat 2/14

5:59 pm-11:12 pm

1 stop4h 13m

Montreal Pierre Elliott Trudeau Intl

Sat 2/21

6:00 am-12:35 pm

1 stop7h 35m

$236

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Tue 2/17

6:00 am-5:04 pm

1 stop10h 04m

Montreal Pierre Elliott Trudeau Intl

Wed 2/25

6:00 am-12:35 pm

1 stop7h 35m

$236

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Wed 2/18

1:05 pm-11:54 pm

1 stop9h 49m

Montreal Pierre Elliott Trudeau Intl

Sat 2/21

6:00 am-12:35 pm

1 stop7h 35m

$236

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sat 2/14

5:59 pm-11:12 pm

1 stop4h 13m

Montreal Pierre Elliott Trudeau Intl

Tue 2/24

7:00 am-4:25 pm

1 stop10h 25m

$236

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Tue 2/17

6:00 am-5:04 pm

1 stop10h 04m

Montreal Pierre Elliott Trudeau Intl

Sat 2/21

6:00 am-12:35 pm

1 stop7h 35m

$236

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 2/12

1:05 pm-11:54 pm

1 stop9h 49m

Montreal Pierre Elliott Trudeau Intl

Sun 2/15

7:00 am-3:25 pm

1 stop9h 25m

$236

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 1/29

1:05 pm-11:54 pm

1 stop9h 49m

Montreal Pierre Elliott Trudeau Intl

Sun 2/1

6:00 am-12:35 pm

1 stop7h 35m

$236

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sun 2/15

4:15 pm-10:45 pm

1 stop5h 30m

Montreal Pierre Elliott Trudeau Intl

Sun 2/22

11:25 am-3:20 pm

1 stop4h 55m

$299

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 11/20

4:15 pm-10:45 pm

1 stop5h 30m

Montreal Pierre Elliott Trudeau Intl

Fri 11/21

6:45 am-10:05 am

1 stop4h 20m

$314

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Mon 11/17

9:27 am-12:43 am

2 stops38h 16m

$140

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 19 results
1
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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 October.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Montreal flight deals on Cheapflights vs. FlightHub >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 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 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
No data available for this route at this time. Please check back soon.

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 October 14, 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
379 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.0

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
8.0
Very good
379 reviews
Porter Airlines
8.0
Very good
379 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.0

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 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 13m. The distance between Chicago Midway Airport and Montreal is about 743 mi.

  • 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

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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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$249Average$438FlexibilityNo cancel feeOn-time52%

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