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Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport from C$ 179

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 6/5. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — MDW
20 Apr — 27 Apr1
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 15 April 2025.

Round-trip from

C$ 325

One-way from

C$ 179

Popular in

October

Cheapest in

May

Average price

C$ 378
Porter Airlines
  • Porter Airlines
  • 1/5-4/5
  • 2 total stops
  • 9h 34m total
  • Montreal to Chicago
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Porter Airlines
  • Porter Airlines
  • 6/5
  • 1 total stop
  • 4h 14m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (C$ 58 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 April 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 15 April 2025.

Fri 9/51:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Mon 12/59:40 a.m.MDW - YUL
1 stop5h 20mPorter Airlines
Deal found 15/4C$ 321
Thu 8/56:00 a.m.YUL - MDW
1 stop3h 40mDelta
Sun 11/56:25 p.m.MDW - YUL
1 stop3h 51mDelta
Deal found 15/4C$ 350
Sun 15/66:45 p.m.YUL - MDW
1 stop28h 00mMultiple Airlines
Thu 19/65:20 p.m.MDW - YUL
1 stop3h 55mMultiple Airlines
Deal found 14/4C$ 428
Sat 17/57:00 a.m.YUL - MDW
1 stop15h 14mWestJet
Fri 30/59:20 a.m.MDW - YUL
2 stops14h 23mWestJet
Deal found 15/4C$ 466

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 15 April 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

Fri 9/5

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

1 stop4h 14m

Chicago Midway

Mon 12/5

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

1 stop5h 20m

C$ 321

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 8/5

6:00 a.m.-8:40 a.m.

1 stop3h 40m

Chicago Midway

Sun 11/5

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

1 stop3h 51m

C$ 350

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 15/6

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

1 stop28h 00m

Chicago Midway

Thu 19/6

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

1 stop3h 55m

C$ 428

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

Fri 30/5

9:20 a.m.-12:43 a.m.

2 stops14h 23m

C$ 466

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 6/5

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

1 stop4h 14m

C$ 179

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 31/5

12:56 p.m.-4:21 p.m.

1 stop4h 25m

C$ 221

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 6/6

6:45 a.m.-9:27 p.m.

2 stops15h 42m

C$ 284

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 15/7

11:15 a.m.-11:21 p.m.

2 stops13h 06m

C$ 533

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/4

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, January 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$ 243). 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.

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 15 April 2025.
Read through reviews of airlines operating flights from Montreal to Chicago, such as Porter Airlines, Delta and WestJet. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
281 reviews
Check prices

Boarding

8.2

Crew

8.7

Overall

8.0

Comfort

8.0

Entertainment

7.0

Food

7.6

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Porter Airlines
8.0
Very good
281 reviews
Porter Airlines
8.0
Very good
281 reviews
Check prices

Boarding

8.2

Crew

8.7

Overall

8.0

Comfort

8.0

Entertainment

7.0

Food

7.6

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
Delta
8.0
Very good
7,918 reviews
Porter Airlines
8.0
Very good
281 reviews
Check prices

Boarding

8.2

Crew

8.7

Overall

8.0

Comfort

8.0

Entertainment

7.0

Food

7.6

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?
WestJet
7.2
Good
2,805 reviews
Porter Airlines
8.0
Very good
281 reviews
Check prices

Boarding

8.2

Crew

8.7

Overall

8.0

Comfort

8.0

Entertainment

7.0

Food

7.6

Reviews

1 / 17
10.0
Excellent

Anonymous,Dec 2024

YYZ - LAS

Everything about the rescheduled (cost me $180) flight great. ***Being denied boarding because I was few minutes under 1.5 hours was not. Stuck at the Kiosk for about 15 minutes before it directed me to the Porter counter was strange. Do not know why checking in online at home was not successful? I think something was up...what can you do?

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$ 325 on this airline. Additional options worth looking into are Delta and WestJet, starting at C$ 345 and C$ 466 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$ 179), Delta (C$ 221), and WestJet (C$ 284).

  • 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, January 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$ 243). 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 15 April 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 333AverageC$ 428FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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How does Cheapflights help users find flights from Pierre Elliott Trudeau Intl to Midway?

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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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