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Cheap flights from Montreal to Chicago Midway Airport from C$ 223

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 20/4. Fares are subject to change and may not be available on all flights or dates of travel.
YMQ — MDW
8 Apr — 15 Apr1
1 adult

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 3 April 2025.

Round-trip from

C$ 349

One-way from

C$ 223

Popular in

October

Cheapest in

September

Average price

C$ 388
Porter Airlines
  • Porter Airlines
  • 27/6-29/6
  • 2 total stops
  • 10h 04m total
  • Montreal to Chicago
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Porter Airlines
  • Porter Airlines
  • 20/4
  • 1 total stop
  • 4h 30m total
  • Montreal to Chicago
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Highest demand for flights based on searches. 4% potential increase in price (C$ 33 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 25 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Montreal to Midway

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 3 April 2025.

Fri 27/61:10 p.m.YUL - MDW
1 stop4h 44mPorter Airlines
Sun 29/69:40 a.m.MDW - YUL
1 stop5h 20mPorter Airlines
Deal found 2/4C$ 349
Fri 2/512:38 p.m.YUL - MDW
1 stop10h 44mDelta
Fri 9/56:25 p.m.MDW - YUL
1 stop3h 51mDelta
Deal found 2/4C$ 360
Sat 10/52:50 p.m.YUL - MDW
1 stop7h 24mMultiple Airlines
Mon 12/59:40 a.m.MDW - YUL
1 stop5h 20mMultiple Airlines
Deal found 2/4C$ 408
Sat 17/57:00 a.m.YUL - MDW
1 stop15h 14mWestJet
Sat 24/57:25 p.m.MDW - YUL
1 stop26h 54mWestJet
Deal found 2/4C$ 466

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 3 April 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 27/6

1:10 p.m.-4:54 p.m.

1 stop4h 44m

Chicago Midway

Sun 29/6

9:40 a.m.-4:00 p.m.

1 stop5h 20m

C$ 349

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 2/5

12:38 p.m.-10:22 p.m.

1 stop10h 44m

Chicago Midway

Fri 9/5

6:25 p.m.-11:16 p.m.

1 stop3h 51m

C$ 360

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 10/5

2:50 p.m.-9:14 p.m.

1 stop7h 24m

Chicago Midway

Mon 12/5

9:40 a.m.-4:00 p.m.

1 stop5h 20m

C$ 408

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 17/5

7:00 a.m.-9:14 p.m.

1 stop15h 14m

Chicago Midway

Sat 24/5

7:25 p.m.-11:19 p.m.

1 stop26h 54m

C$ 466

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 20/4

6:50 a.m.-10:20 a.m.

1 stop4h 30m

C$ 223

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 11/6

10:45 a.m.-7:31 p.m.

2 stops9h 46m

C$ 309

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 7/7

6:15 p.m.-9:47 p.m.

1 stop28h 32m

C$ 330

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

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, January is the cheapest month in which you can book a flight from Montreal to Chicago Midway Airport (average of C$ 243). Flying from Montreal to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 43.0 mm.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 3 April 2025.
Peruse reviews from past customers who have flown with Delta, Porter Airlines and WestJet from Montreal to Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,897 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Overall

8.0

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Delta
8.0
Very good
7,897 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Overall

8.0

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
Porter Airlines
7.9
Good
279 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Overall

8.0

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception
WestJet
7.2
Good
2,795 reviews
Delta
8.0
Very good
7,897 reviews
Check prices

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Overall

8.0

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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.

  • What are the cheapest airlines flying from Montreal to Chicago Midway Airport round-trip?

    Porter Airlines, at C$ 349, was found to be the cheapest airline from Montreal to Chicago Midway Airport.Alternate airlines to your destination round-trip include Delta and WestJet. You may be able to fly from Montreal to Chicago Midway Airport for 26% less than the average price by searching for these airlines.

  • 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, January is the cheapest month in which you can book a flight from Montreal to Chicago Midway Airport (average of C$ 243). Flying from Montreal to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). 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 3 April 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 343AverageC$ 440FlexibilityNo 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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