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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 12/26. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YMQ
Dec 4 — Dec 111
Thu 12/4
Thu 12/11
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 November 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$236
(Delta)

One-way from

$137
(Trip.com)

Popular in

December

Cheapest in

September

Average price

$337
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. 2% potential increase in price ($8 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 4, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/54:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Sun 12/76:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 11/2$282
This Trip.com deal was found by Cheapflights users on 11/3. 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 12/124:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Sun 12/146:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 11/3$287
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/211:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Fri 12/511:25 amYUL - MDW
1 stop4h 55mPorter Airlines
Deal found 11/2$288
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/111:00 amMDW - YUL
1 stop5h 45mPorter Airlines
Wed 12/36:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 11/2$289
This Trip.com deal was found by Cheapflights users on 11/2. 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.
Sat 12/612:45 pmMDW - YUL
1 stop5h 00mPorter Airlines
Sun 12/76:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 11/2$290
This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/3011:00 amMDW - YUL
1 stop5h 45mPorter Airlines
Sat 1/311:25 amYUL - MDW
1 stop4h 55mPorter Airlines
Deal found 11/3$292
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1811:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Thu 12/2510:15 amYUL - MDW
1 stop6h 05mPorter Airlines
Deal found 11/2$293
This Trip.com deal was found by Cheapflights users on 11/2. 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.
Sun 12/2111:00 amMDW - YUL
1 stop4h 30mPorter Airlines
Mon 12/2910:15 amYUL - MDW
1 stop6h 05mPorter Airlines
Deal found 11/2$295
This Trip.com deal was found by Cheapflights users on 11/3. 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.
Thu 12/114:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Sun 12/146:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 11/3$296
This Mytrip deal was found by Cheapflights users on 11/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/612:45 pmMDW - YUL
1 stop5h 00mPorter Airlines
Mon 12/86:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 11/2$303
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
Mon 12/14:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Thu 12/46:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 11/3$304

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 November 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

Thu 3/26

11:00 am-6:45 pm

1 stop6h 45m

Montreal Pierre Elliott Trudeau Intl

Thu 4/2

6:45 am-10:05 am

1 stop4h 20m

$220

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 1/30

6:00 am-4:57 pm

1 stop9h 57m

Montreal Pierre Elliott Trudeau Intl

Wed 2/4

12:54 pm-5:55 pm

1 stop6h 01m

$236

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sat 2/14

1:28 pm-11:12 pm

1 stop8h 44m

Montreal Pierre Elliott Trudeau Intl

Sat 2/21

6:00 am-12:48 pm

1 stop7h 48m

$236

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Mon 2/16

9:34 am-3:55 pm

1 stop5h 21m

Montreal Pierre Elliott Trudeau Intl

Fri 2/20

6:00 am-12:48 pm

1 stop7h 48m

$236

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sat 3/28

5:59 pm-11:12 pm

1 stop4h 13m

Montreal Pierre Elliott Trudeau Intl

Wed 4/1

6:00 am-12:35 pm

1 stop7h 35m

$236

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sat 3/28

5:59 pm-11:12 pm

1 stop4h 13m

Montreal Pierre Elliott Trudeau Intl

Sat 4/4

6:00 am-12:35 pm

1 stop7h 35m

$236

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Tue 2/17

1:28 pm-11:12 pm

1 stop8h 44m

Montreal Pierre Elliott Trudeau Intl

Sat 2/21

7:00 am-3:23 pm

1 stop9h 23m

$236

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 2/26

11:00 am-5:45 pm

1 stop5h 45m

Montreal Pierre Elliott Trudeau Intl

Sun 3/1

11:25 am-3:20 pm

1 stop4h 55m

$244

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 4/3

11:00 am-5:45 pm

1 stop5h 45m

Montreal Pierre Elliott Trudeau Intl

Thu 4/9

11:25 am-3:20 pm

1 stop4h 55m

$255

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Mon 3/30

11:00 am-4:30 pm

1 stop4h 30m

Montreal Pierre Elliott Trudeau Intl

Sat 4/4

8:55 am-11:50 am

1 stop3h 55m

$258

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/4

Showing 1-10 of 22 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 November.
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
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 November 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
387 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.6

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Porter Airlines
8.0
Very good
387 reviews
Porter Airlines
8.0
Very good
387 reviews

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.6

Entertainment

7.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

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 6h 45m. 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

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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 November 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$249Average$457FlexibilityNo cancel feeOn-time52%

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