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$108+ 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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — YMQ
May 3 — May 101
Sun 5/3
Sun 5/10
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 April 3, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/1. 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.
Fri 5/2910:30 am
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Tue 6/26:30 am
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Deal found 4/1$261
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 4/237:30 am
MDW
-
YUL
1 stop7h 55m
Multiple Airlines
Sun 4/269:50 am
YUL
-
MDW
1 stop6h 30m
Multiple Airlines
Deal found 4/1$266
This Trip.com deal was found by Cheapflights users on 3/30. 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 4/2311:00 am
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Fri 5/16:30 am
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Deal found 3/30$267
This Kiwi.com deal was found by Cheapflights users on 4/2. 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 4/277:30 am
MDW
-
YUL
1 stop7h 55m
Multiple Airlines
Fri 5/16:30 am
YUL
-
MDW
1 stop4h 15m
Multiple Airlines
Deal found 4/2$269
This Trip.com deal was found by Cheapflights users on 3/29. 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 4/174:05 pm
MDW
-
YUL
1 stop5h 40m
Porter Airlines
Sun 4/199:50 am
YUL
-
MDW
1 stop6h 30m
Porter Airlines
Deal found 3/29$270
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 4/207:30 am
MDW
-
YUL
1 stop7h 55m
Multiple Airlines
Thu 4/238:55 am
YUL
-
MDW
2 stops29h 05m
Multiple Airlines
Deal found 3/29$275
This Trip.com deal was found by Cheapflights users on 3/29. 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 5/53:20 pm
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Thu 5/76:30 am
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Deal found 3/29$276
This Vliegwinkel deal was found by Cheapflights users on 3/31. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/83:20 pm
MDW
-
YUL
1 stop3h 50m
Porter Airlines
Mon 5/116:30 am
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Deal found 3/31$278
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 4/287:30 am
MDW
-
YUL
2 stops30h 40m
Multiple Airlines
Tue 5/510:35 am
YUL
-
MDW
1 stop5h 00m
Multiple Airlines
Deal found 3/31$279
This Kiwi.com deal was found by Cheapflights users on 4/2. 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.
Sun 5/310:30 am
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Mon 5/1110:35 am
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Deal found 4/2$280

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 April 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$261
(Kiwi.com)

One-way from

$108
(CheapTickets)

Popular in

June

Cheapest in

February

Average price

$482
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. 17% potential increase in price ($76 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
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 April 3, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Montreal that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Tue 5/19

6:23 am-5:43 pm

1 stop10h 20m

Montreal Pierre Elliott Trudeau Intl

Sun 5/24

6:00 am-8:43 am

1 stop3h 43m

$325

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 6/19

5:11 pm-11:59 pm

1 stop5h 48m

Montreal Pierre Elliott Trudeau Intl

Mon 6/22

6:00 am-12:36 pm

1 stop7h 36m

$325
Quickest round-trip

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 4/17

6:38 pm-11:19 pm

1 stop3h 41m

Montreal Pierre Elliott Trudeau Intl

Sun 4/19

7:00 am-1:32 pm

1 stop7h 32m

$325

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Mon 5/25

6:23 am-5:43 pm

1 stop10h 20m

Montreal Pierre Elliott Trudeau Intl

Fri 6/5

12:40 pm-9:09 pm

1 stop9h 29m

$325

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 4/17

9:27 am-4:15 pm

1 stop5h 48m

Montreal Pierre Elliott Trudeau Intl

Mon 4/20

6:00 am-12:43 pm

1 stop7h 43m

$325

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Thu 6/4

12:53 pm-11:57 pm

1 stop10h 04m

Montreal Pierre Elliott Trudeau Intl

Sun 6/7

6:00 am-9:14 am

1 stop4h 14m

$325

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Tue 4/21

5:21 pm-11:51 pm

1 stop5h 30m

Montreal Pierre Elliott Trudeau Intl

Thu 4/30

12:42 pm-10:28 pm

1 stop10h 46m

$325

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 4/17

1:24 pm-11:19 pm

1 stop8h 55m

Montreal Pierre Elliott Trudeau Intl

Tue 4/21

12:42 pm-10:28 pm

1 stop10h 46m

$325

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Fri 5/1

1:24 pm-11:19 pm

1 stop8h 55m

Montreal Pierre Elliott Trudeau Intl

Sun 5/3

7:00 am-4:26 pm

1 stop10h 26m

$325
Cheapest one-way

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Mon 5/11

10:30 am-5:15 pm

1 stop5h 45m

$108

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

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 April.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
Trip.comPrice Accuracy1 starTrust 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

How often are flights from Chicago to Montreal delayed?

About 36% of weekly flights between Chicago and Montreal have experienced delays in the past year, with the average delay time being 60 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.

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 April 3, 2026.
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
430 reviews

Comfort

8.0

Entertainment

7.0

Food

7.6

Crew

8.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
430 reviews
Porter Airlines
8.0
Very good
430 reviews

Comfort

8.0

Entertainment

7.0

Food

7.6

Crew

8.6

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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 10h 20m. The distance between Chicago Midway Airport and Montreal is about 743 mi.

  • 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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