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Cheap flights from Montreal to Chicago Midway Airport from C$ 157

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 19/3. Fares are subject to change and may not be available on all flights or dates of travel.
YMQ — MDW
23 Mar — 30 Mar1
1 adult
1 adult, Economy, 0 bags

Cheap 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 21 February 2026.

Thu 19/36:50 a.m.
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Thu 26/311:00 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 19/2C$ 228
Tue 28/46:50 a.m.
YUL
-
MDW
1 stop4h 25m
Porter Airlines
Mon 4/510:25 a.m.
MDW
-
YUL
1 stop6h 50m
Porter Airlines
Deal found 19/2C$ 230
Wed 20/51:00 p.m.
YUL
-
MDW
1 stop4h 50m
Porter Airlines
Wed 27/510:25 a.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 21/2C$ 234
Wed 1/46:50 a.m.
YUL
-
MDW
1 stop4h 25m
Porter Airlines
Mon 6/411:00 a.m.
MDW
-
YUL
1 stop4h 30m
Porter Airlines
Deal found 19/2C$ 235
Mon 6/46:50 a.m.
YUL
-
MDW
1 stop4h 25m
Porter Airlines
Mon 13/411:00 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 20/2C$ 241
Thu 16/46:50 a.m.
YUL
-
MDW
1 stop4h 25m
Porter Airlines
Thu 23/411:00 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 19/2C$ 246
Thu 26/36:50 a.m.
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Mon 30/311:00 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 21/2C$ 253
Fri 10/48:55 a.m.
YUL
-
MDW
1 stop7h 25m
Porter Airlines
Mon 13/411:00 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 21/2C$ 257
Fri 8/56:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Sun 10/510:25 a.m.
MDW
-
YUL
1 stop8h 45m
Porter Airlines
Deal found 18/2C$ 260
Mon 13/46:50 a.m.
YUL
-
MDW
1 stop4h 25m
Porter Airlines
Thu 16/411:00 a.m.
MDW
-
YUL
1 stop7h 15m
Porter Airlines
Deal found 18/2C$ 261
Thu 21/51:00 p.m.
YUL
-
MDW
1 stop4h 50m
Porter Airlines
Sun 24/510:25 a.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 18/2C$ 267
Mon 18/56:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Tue 26/510:25 a.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 20/2C$ 278

Find 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 21 February 2026.

Round-trip from

C$ 228

One-way from

C$ 157

Popular in

November

Cheapest in

September

Average price

C$ 250
Porter Airlines
  • Porter Airlines
  • 19/3-26/3
  • 2 total stops
  • 10h 00m total
  • Montreal to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 19/3
  • 1 total stop
  • 4h 35m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 116 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 21 February 2026.
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

Thu 26/3

6:50 a.m.-10:05 a.m.

1 stop4h 15m

Chicago Midway

Mon 30/3

11:00 a.m.-5:45 p.m.

1 stop5h 45m

C$ 253

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 14/3

6:00 a.m.-12:29 p.m.

1 stop7h 29m

Chicago Midway

Mon 16/3

6:34 p.m.-11:13 p.m.

1 stop3h 39m

C$ 287

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 12/3

6:00 a.m.-12:29 p.m.

1 stop7h 29m

Chicago Midway

Mon 16/3

6:34 p.m.-11:13 p.m.

1 stop3h 39m

C$ 300

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 1/5

7:00 a.m.-4:26 p.m.

1 stop10h 26m

Chicago Midway

Mon 4/5

6:00 a.m.-5:34 p.m.

1 stop10h 34m

C$ 300

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 19/3

6:00 a.m.-12:29 p.m.

1 stop7h 29m

Chicago Midway

Tue 24/3

12:47 p.m.-11:45 p.m.

1 stop9h 58m

C$ 300

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 23/3

6:00 a.m.-12:29 p.m.

1 stop7h 29m

Chicago Midway

Mon 30/3

9:35 a.m.-3:53 p.m.

1 stop5h 18m

C$ 300

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 19/5

6:00 a.m.-12:42 p.m.

1 stop7h 42m

Chicago Midway

Wed 27/5

6:36 p.m.-11:13 p.m.

1 stop3h 37m

C$ 300

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 11/4

6:00 a.m.-12:29 p.m.

1 stop7h 29m

Chicago Midway

Mon 13/4

5:21 p.m.-11:51 p.m.

1 stop5h 30m

C$ 300

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 18/5

7:00 a.m.-4:17 p.m.

1 stop10h 17m

Chicago Midway

Mon 25/5

1:22 p.m.-11:13 p.m.

1 stop8h 51m

C$ 300

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 15/3

6:00 a.m.-12:29 p.m.

1 stop7h 29m

Chicago Midway

Tue 17/3

12:47 p.m.-11:45 p.m.

1 stop9h 58m

C$ 300

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/2

Showing 1-10 of 22 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
No data available for this route at this time. Please check back soon.

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 21 February 2026.
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
419 reviews
Check prices

Crew

8.6

Boarding

8.2

Entertainment

6.9

Overall

8.0

Food

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!
Porter Airlines
8.0
Very good
419 reviews
Porter Airlines
8.0
Very good
419 reviews
Check prices

Crew

8.6

Boarding

8.2

Entertainment

6.9

Overall

8.0

Food

7.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Feb 2026

YYJ - YYZ

Always great! The Flight Attendants are always polite and attentive! The Polite was great and reminded us all that it was Valentine's Day!

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 15m. The time it takes to get you to your destination can typically vary by up to 3h 14m. 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$ 187, 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.

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 21 February 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 187AverageC$ 377FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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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