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Cheap flights from Montreal to Chicago Midway Airport from C$ 202

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 14/7. Fares are subject to change and may not be available on all flights or dates of travel.
YMQ — MDW
17 Jun — 24 Jun1
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 12 June 2025.

Round-trip from

C$ 309

One-way from

C$ 202

Popular in

October

Cheapest in

April

Average price

C$ 525
Porter Airlines
  • Porter Airlines
  • 11/7-13/7
  • 2 total stops
  • 9h 34m total
  • Montreal to Chicago
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Porter Airlines
  • Porter Airlines
  • 14/7
  • 1 total stop
  • 4h 14m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 3% potential increase in price (C$ 22 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 23 potential savings vs. average RT price).
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Average for round-trip flights in June 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 12 June 2025.

Fri 11/71:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Sun 13/79:40 a.m.MDW - YUL
1 stop5h 20mPorter Airlines
Deal found 10/6C$ 309
Fri 3/107:00 a.m.YUL - MDW
1 stop10h 23mDelta
Wed 8/109:30 a.m.MDW - YUL
1 stop5h 30mDelta
Deal found 10/6C$ 324
Sat 11/107:00 a.m.YUL - MDW
1 stop15h 44mMultiple Airlines
Wed 15/109:15 a.m.MDW - YUL
1 stop8h 30mMultiple Airlines
Deal found 10/6C$ 436
Fri 3/106:15 p.m.YUL - MDW
1 stop28h 29mWestJet
Wed 8/101:05 p.m.MDW - YUL
2 stops10h 32mWestJet
Deal found 12/6C$ 487

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 12 June 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 11/7

1:10 p.m.-4:24 p.m.

1 stop4h 14m

Chicago Midway

Sun 13/7

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

1 stop5h 20m

C$ 309

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 3/10

7:00 a.m.-4:23 p.m.

1 stop10h 23m

Chicago Midway

Wed 8/10

9:30 a.m.-4:00 p.m.

1 stop5h 30m

C$ 324

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 11/10

7:00 a.m.-9:44 p.m.

1 stop15h 44m

Chicago Midway

Wed 15/10

9:15 a.m.-6:45 p.m.

1 stop8h 30m

C$ 436

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 3/10

6:45 a.m.-9:44 p.m.

2 stops15h 59m

Chicago Midway

Wed 8/10

1:05 p.m.-12:37 a.m.

2 stops10h 32m

C$ 485

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 14/7

1:10 p.m.-4:24 p.m.

1 stop4h 14m

C$ 202

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 11/10

7:00 a.m.-3:30 p.m.

1 stop9h 30m

C$ 216

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 13/7

6:45 a.m.-8:45 a.m.

1 stop27h 00m

C$ 271

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 11/10

7:00 a.m.-9:44 p.m.

1 stop15h 44m

C$ 295

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/6

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 12 June 2025.
Peruse reviews from past customers who have flown with Porter Airlines, Delta 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.
Porter Airlines
8.0
Very good
288 reviews
Check prices

Crew

8.7

Overall

8.0

Boarding

8.2

Comfort

8.1

Food

7.6

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
288 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Crew

8.7

Overall

8.0

Boarding

8.2

Comfort

8.1

Food

7.6

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,946 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Crew

8.7

Overall

8.0

Boarding

8.2

Comfort

8.1

Food

7.6

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
WestJet
7.2
Good
2,868 reviews
Porter Airlines
8.0
Very good
288 reviews
Check prices

Crew

8.7

Overall

8.0

Boarding

8.2

Comfort

8.1

Food

7.6

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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$ 309, 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 32% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Montreal to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as C$ 202 on Porter Airlines. Other airlines that offer cheap prices include Delta from C$ 216 and WestJet from C$ 295 one-way.

  • 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 12 June 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 296AverageC$ 427FlexibilityNo 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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