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$101+ 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 10/24. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YMQ
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$232
(Kiwi.com)

One-way from

$101
(iWofly)

Popular in

December

Cheapest in

September

Average price

$310
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. 3% potential increase in price ($12 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 September 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 September 11, 2025.

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.
Thu 10/235:20 pmMDW - YUL
1 stop3h 55mPorter Airlines
Mon 10/276:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 9/9$232
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 10/245:20 pmMDW - YUL
1 stop3h 55mPorter Airlines
Sun 10/266:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 9/9$235
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 10/75:20 pmMDW - YUL
1 stop3h 55mPorter Airlines
Tue 10/1410:45 amYUL - MDW
1 stop6h 39mPorter Airlines
Deal found 9/9$238
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.
Thu 12/44:15 pmMDW - YUL
1 stop5h 30mPorter Airlines
Tue 12/96:45 amYUL - MDW
1 stop4h 20mPorter Airlines
Deal found 9/9$240
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.
Mon 10/209:35 amMDW - YUL
1 stop5h 25mPorter Airlines
Thu 10/231:10 pmYUL - MDW
1 stop4h 14mPorter Airlines
Deal found 9/9$242
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.
Thu 10/95:20 pmMDW - YUL
1 stop3h 55mPorter Airlines
Tue 10/1410:45 amYUL - MDW
1 stop6h 39mPorter Airlines
Deal found 9/9$253
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1311:00 amMDW - YUL
1 stop6h 45mPorter Airlines
Mon 11/1710:15 amYUL - MDW
1 stop6h 05mPorter Airlines
Deal found 9/9$256
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.
Sat 10/189:35 amMDW - YUL
1 stop7h 20mPorter Airlines
Tue 10/211:10 pmYUL - MDW
1 stop4h 14mPorter Airlines
Deal found 9/9$259
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.
Sat 10/119:35 amMDW - YUL
1 stop7h 20mPorter Airlines
Wed 10/151:10 pmYUL - MDW
1 stop4h 14mPorter Airlines
Deal found 9/9$260
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 10/155:20 pmMDW - YUL
1 stop3h 55mPorter Airlines
Sun 10/198:55 amYUL - MDW
1 stop8h 29mPorter Airlines
Deal found 9/9$262

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 September 11, 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 10/23

5:20 pm-10:15 pm

1 stop3h 55m

Montreal Pierre Elliott Trudeau Intl

Mon 10/27

11:25 am-3:20 pm

1 stop4h 55m

$234

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Tue 10/7

5:20 pm-10:15 pm

1 stop3h 55m

Montreal Pierre Elliott Trudeau Intl

Tue 10/14

10:45 am-4:24 pm

1 stop6h 39m

$238

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sat 10/18

9:35 am-5:55 pm

1 stop7h 20m

Montreal Pierre Elliott Trudeau Intl

Tue 10/21

1:10 pm-4:24 pm

1 stop4h 14m

$259

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sat 10/18

9:35 am-5:55 pm

1 stop7h 20m

Montreal Pierre Elliott Trudeau Intl

Wed 10/22

10:45 am-4:24 pm

1 stop6h 39m

$260

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sat 10/11

9:35 am-5:55 pm

1 stop7h 20m

Montreal Pierre Elliott Trudeau Intl

Tue 10/14

10:45 am-4:24 pm

1 stop6h 39m

$260

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 10/23

9:35 am-4:00 pm

1 stop5h 25m

Montreal Pierre Elliott Trudeau Intl

Sun 10/26

6:45 am-10:05 am

1 stop4h 20m

$264

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Sun 10/12

5:20 pm-10:15 pm

1 stop3h 55m

Montreal Pierre Elliott Trudeau Intl

Wed 10/15

1:10 pm-4:24 pm

1 stop4h 14m

$264

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 10/30

4:15 pm-10:45 pm

1 stop5h 30m

Montreal Pierre Elliott Trudeau Intl

Sun 11/2

5:45 am-9:05 am

1 stop4h 20m

$265

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Mon 10/20

5:20 pm-10:15 pm

1 stop3h 55m

Montreal Pierre Elliott Trudeau Intl

Thu 10/23

10:45 am-4:24 pm

1 stop6h 39m

$265

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Wed 12/3

11:00 am-5:45 pm

1 stop5h 45m

Montreal Pierre Elliott Trudeau Intl

Thu 12/11

6:45 am-10:05 am

1 stop4h 20m

$266

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 19 results
1
2

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 September 11, 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
7.9
Good
363 reviews

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.6

Food

7.6

Entertainment

7.0

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

Overall

7.9

Comfort

7.9

Boarding

8.1

Crew

8.6

Food

7.6

Entertainment

7.0

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 3h 55m. 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 $245, 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Montreal?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Montreal (average of $270). Flying from Chicago Midway Airport to Montreal in July is currently the most expensive (average of $409). 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

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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapest$245Average$391FlexibilityNo cancel feeOn-time52%

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