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Cheap flights from Montreal to Chicago Midway Airport from C$ 228

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 13/1. Fares are subject to change and may not be available on all flights or dates of travel.
YMQ — MDW
29 Dec — 5 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Montreal to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Montreal (YMQ) to Midway (MDW). 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 29 November 2025.

Round-trip from

C$ 275

One-way from

C$ 228

Popular in

November

Cheapest in

September

Average price

C$ 570
Porter Airlines
  • Porter Airlines
  • 19/12-2/1
  • 2 total stops
  • 9h 50m total
  • Montreal to Chicago
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13/1
  • 13/1
  • 2 total stops
  • 16h 07m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 114 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 23 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 Montreal to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Montreal to Midway
Explore the most affordable flight options available from Montreal to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 29 November 2025.

Fri 19/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Fri 2/14:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 28/11C$ 275
Sun 21/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Sat 3/111:05 a.m.MDW - YUL
1 stop4h 25mPorter Airlines
Deal found 28/11C$ 279
Sat 27/1211:25 a.m.YUL - MDW
1 stop4h 55mPorter Airlines
Mon 23/211:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 28/11C$ 300
Mon 29/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Tue 6/111:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 27/11C$ 301
Fri 19/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Sun 4/111:00 a.m.MDW - YUL
1 stop5h 45mPorter Airlines
Deal found 27/11C$ 319
Tue 30/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Fri 2/14:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 28/11C$ 324
Tue 30/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Sun 4/111:00 a.m.MDW - YUL
1 stop5h 45mPorter Airlines
Deal found 28/11C$ 325
Sat 20/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Tue 6/111:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 28/11C$ 331
Thu 25/1210:15 a.m.YUL - MDW
1 stop6h 05mPorter Airlines
Sun 28/124:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 28/11C$ 336
Mon 22/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Sat 3/111:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 28/11C$ 338

Cheapflights Fare Finder

 
Customize your flight search to find flights from Montreal to Midway 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 629,999 searches. Data last updated 29 November 2025.
Use the filters below to find and compare flights from Montreal to Chicago Midway Airport that are best for you.

Fly from

Montreal

Fly to

Midway

Route

Depart

Return

Price

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 27/2

6:45 a.m.-10:10 a.m.

1 stop4h 25m

Chicago Midway

Sun 8/3

4:15 p.m.-10:45 p.m.

1 stop5h 30m

C$ 294

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 15/4

7:00 a.m.-4:25 p.m.

1 stop10h 25m

Chicago Midway

Sun 19/4

6:00 a.m.-5:07 p.m.

1 stop10h 07m

C$ 301

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 29/12

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

Tue 6/1

11:00 a.m.-4:30 p.m.

1 stop4h 30m

C$ 301

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 26/2

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

Sat 7/3

12:45 p.m.-6:45 p.m.

1 stop5h 00m

C$ 305

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 20/1

6:00 a.m.-12:51 p.m.

1 stop7h 51m

Chicago Midway

Mon 9/3

2:03 p.m.-11:40 p.m.

1 stop8h 37m

C$ 310

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 22/1

6:00 a.m.-12:46 p.m.

1 stop7h 46m

Chicago Midway

Mon 9/3

2:03 p.m.-11:40 p.m.

1 stop8h 37m

C$ 310

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 24/1

6:00 a.m.-12:46 p.m.

1 stop7h 46m

Chicago Midway

Thu 5/3

9:34 a.m.-3:55 p.m.

1 stop5h 21m

C$ 310

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 26/1

6:00 a.m.-12:46 p.m.

1 stop7h 46m

Chicago Midway

Tue 3/3

6:17 p.m.-11:10 p.m.

1 stop3h 53m

C$ 310

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 13/1

7:00 a.m.-4:29 p.m.

1 stop10h 29m

Chicago Midway

Tue 20/1

6:35 p.m.-11:12 p.m.

1 stop3h 37m

C$ 310

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 17/1

7:00 a.m.-4:29 p.m.

1 stop10h 29m

Chicago Midway

Mon 19/1

10:46 a.m.-4:55 p.m.

1 stop5h 09m

C$ 310

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/11

Showing 1-10 of 21 results
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Best time to book a flight from Montreal to Midway

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

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

Currently, September is the cheapest month in which you can book a flight from Montreal to Chicago Midway Airport (average of C$ 184). Flying from Montreal to Chicago Midway Airport in January is currently the most expensive (average of C$ 420). 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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated 29 November 2025.
Read through reviews of airlines operating flights from Montreal to Chicago Midway Airport, such as Porter Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
394 reviews
Check prices

Crew

8.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.0

Food

7.6

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
Check prices

Crew

8.6

Boarding

8.2

Comfort

8.0

Overall

8.0

Entertainment

7.0

Food

7.6

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 Montreal to Midway. 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 Montreal to Chicago Midway Airport?

    Airlines like Porter Airlines and Delta fly from Montreal to Chicago Midway Airport in about 4h 25m. The time it takes to get you to your destination can typically vary by up to 6h. Montreal and Chicago Midway Airport are separated by a distance of 1196 km. This flight may include one or multiple stops.

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

    Porter Airlines, at C$ 199, was found to be the cheapest airline from Montreal to Chicago Midway Airport.. You may be able to fly from Montreal to Chicago Midway Airport for 51% less than the average price by searching for this airline.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Montreal to Midway 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 Montreal to Chicago Midway Airport?

    Currently, September is the cheapest month in which you can book a flight from Montreal to Chicago Midway Airport (average of C$ 184). Flying from Montreal to Chicago Midway Airport in January is currently the most expensive (average of C$ 420). 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 Montreal to Midway

Discover the top airline that operate flights from Montreal to Midway. 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 629,999 searches. Data last updated 29 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 199AverageC$ 454FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Montreal to Midway?

Cheapflights makes it easy to find Montreal to Midway flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Montreal to Midway?

Cheapflights helps you find that perfect flight to Midway from Montreal by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Montreal to Midway with no change fees?

Need flexible booking options for your flight to Midway from Montreal? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Montreal to Midway become cheaper?

Yes, Cheapflights offers price alerts on Montreal to Midway flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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