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Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport from C$ 205

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 29/7. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — MDW
5 Jul — 12 Jul1
1 adult

Cheap flight deals from Pierre Elliott Trudeau Intl to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Pierre Elliott Trudeau Intl (YUL) 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 30 June 2025.

Round-trip from

C$ 319

One-way from

C$ 205

Popular in

October

Cheapest in

July

Average price

C$ 446
Porter Airlines
  • Porter Airlines
  • 18/8-26/8
  • 2 total stops
  • 9h 34m total
  • Montreal to Chicago
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Porter Airlines
  • Porter Airlines
  • 29/7
  • 1 total stop
  • 6h 39m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 51 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease (C$ 24 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 Pierre Elliott Trudeau Intl to Midway

Cheapest flights from Pierre Elliott Trudeau Intl to Midway
Explore the most affordable flight options available from Pierre Elliott Trudeau Intl to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 30 June 2025.

Mon 18/81:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Tue 26/89:40 a.m.MDW - YUL
1 stop5h 20mPorter Airlines
Deal found 28/6C$ 319
Sun 31/86:00 a.m.YUL - MDW
1 stop3h 35mDelta
Wed 3/94:25 p.m.MDW - YUL
1 stop6h 28mDelta
Deal found 27/6C$ 347
Thu 24/712:46 p.m.YUL - MDW
1 stop9h 56mMultiple Airlines
Mon 28/75:20 p.m.MDW - YUL
1 stop3h 55mMultiple Airlines
Deal found 29/6C$ 451
Sat 16/86:20 a.m.YUL - MDW
1 stop7h 43mWestJet
Sat 23/81:43 p.m.MDW - YUL
1 stop8h 33mWestJet
Deal found 29/6C$ 454

Cheapflights Fare Finder

Customize your flight search to find flights from Pierre Elliott Trudeau Intl 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 30 June 2025.
Use the filters below to find and compare flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport that are best for you.

Fly from

Pierre Elliott Trudeau Intl

Fly to

Midway

Route

Depart

Return

Price

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 18/8

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

1 stop4h 14m

Chicago Midway

Tue 26/8

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

1 stop5h 20m

C$ 319

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 31/8

6:00 a.m.-8:35 a.m.

1 stop3h 35m

Chicago Midway

Wed 3/9

4:25 p.m.-11:53 p.m.

1 stop6h 28m

C$ 347

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 24/7

12:46 p.m.-9:42 p.m.

1 stop9h 56m

Chicago Midway

Mon 28/7

5:20 p.m.-10:15 p.m.

1 stop3h 55m

C$ 451

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 16/8

6:20 a.m.-1:03 p.m.

1 stop7h 43m

Chicago Midway

Sat 23/8

1:43 p.m.-11:16 p.m.

1 stop8h 33m

C$ 454

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 29/7

10:45 a.m.-4:24 p.m.

1 stop6h 39m

C$ 205

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 9/8

6:20 a.m.-1:06 p.m.

1 stop7h 46m

C$ 241

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 31/7

7:00 a.m.-9:42 p.m.

1 stop15h 42m

C$ 261

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 14/8

6:45 a.m.-7:41 p.m.

2 stops13h 56m

C$ 321

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/6

Best time to book a flight from Pierre Elliott Trudeau Intl to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Pierre Elliott Trudeau Intl 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 Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport

What is the cheapest month to book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

Currently, June is the cheapest month in which you can book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport (average of C$ 238). Flying from Montreal Pierre Elliott Trudeau Intl Airport 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.

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 30 June 2025.
See what other customers who have flown with Porter Airlines,Delta, andWestJet from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
296 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.1

Food

7.6

Crew

8.7

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
296 reviews
Porter Airlines
8.0
Very good
296 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.1

Food

7.6

Crew

8.7

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
7,969 reviews
Porter Airlines
8.0
Very good
296 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.1

Food

7.6

Crew

8.7

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
2,908 reviews
Porter Airlines
8.0
Very good
296 reviews
Check prices

Boarding

8.2

Entertainment

7.0

Overall

8.0

Comfort

8.1

Food

7.6

Crew

8.7

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 Pierre Elliott Trudeau Intl 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 Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport round-trip?

    Our cheapest airline available from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport is Porter Airlines. Our recent data shows that you can find tickets from as low as C$ 319 on this airline. Additional options worth looking into are Delta and WestJet, starting at C$ 347 and C$ 454 round-trip. Users have found that Porter Airlines is 25% cheaper than the other options available to this destination.

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

    The cheapest airlines for a one-way flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport are Porter Airlines (C$ 205), Delta (C$ 241), and WestJet (C$ 261).

  • Can I find deals for flights from Pierre Elliott Trudeau Intl to Midway that include hotel bookings?

    Yes. In addition to deals on Pierre Elliott Trudeau Intl to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Pierre Elliott Trudeau Intl to Midway?

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

  • Can I find deals for business class flights from Pierre Elliott Trudeau Intl to Midway?

    Yes. Cheapflights offers flight deals from Pierre Elliott Trudeau Intl 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 Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

    Currently, June is the cheapest month in which you can book a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport (average of C$ 238). Flying from Montreal Pierre Elliott Trudeau Intl Airport 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

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Alternative routes for Pierre Elliott Trudeau Intl to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Pierre Elliott Trudeau Intl to O'Hare Intl flights

Top airline flying from Pierre Elliott Trudeau Intl to Midway

Discover the top airline that operate flights from Pierre Elliott Trudeau Intl 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 30 June 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 296AverageC$ 443FlexibilityNo cancel feeOn-time52%
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How does Cheapflights help users find flights from Pierre Elliott Trudeau Intl to Midway?

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Yes! Cheapflights helps users easily find flights from Pierre Elliott Trudeau Intl to Midway with no change fees.

Can Cheapflights notify me if prices for flights from Pierre Elliott Trudeau Intl to Midway become cheaper?

Yes, Cheapflights offers price alerts on Pierre Elliott Trudeau Intl 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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