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Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport from C$ 195

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 19/11. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — MDW
17 Oct — 24 Oct1
1 adult
1 adult, Economy

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 17 September 2025.

Round-trip from

C$ 322

One-way from

C$ 195

Popular in

October

Cheapest in

September

Average price

C$ 297
Porter Airlines
  • Porter Airlines
  • 17/10-20/10
  • 2 total stops
  • 9h 39m total
  • Montreal to Chicago
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Porter Airlines
  • Porter Airlines
  • 30/10
  • 1 total stop
  • 4h 20m total
  • Montreal to Chicago
Search Deals
High demand for flights, 1% potential price rise
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Cheapest flight prices on average. 3% potential price decrease (C$ 21 potential savings vs. average RT price).
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Average for round-trip flights in September 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 17 September 2025.

Fri 17/101:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Mon 20/109:35 a.m.MDW - YUL
1 stop5h 25mPorter Airlines
Deal found 15/9C$ 322
Thu 30/106:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Thu 6/114:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 15/9C$ 323
Thu 16/1010:45 a.m.YUL - MDW
1 stop6h 39mPorter Airlines
Sun 19/105:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Deal found 15/9C$ 325
Thu 23/101:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Sun 26/1011:00 a.m.MDW - YUL
1 stop6h 45mPorter Airlines
Deal found 16/9C$ 326
Wed 15/101:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Sun 19/105:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Deal found 14/9C$ 327
Thu 6/116:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Mon 10/1111:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 16/9C$ 333
Fri 31/106:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Fri 7/114:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 16/9C$ 336
Fri 17/101:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Wed 22/109:35 a.m.MDW - YUL
1 stop5h 25mPorter Airlines
Deal found 16/9C$ 337
Wed 8/101:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Thu 16/109:35 a.m.MDW - YUL
1 stop5h 25mPorter Airlines
Deal found 17/9C$ 338
Thu 16/101:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Mon 20/109:35 a.m.MDW - YUL
1 stop5h 25mPorter Airlines
Deal found 17/9C$ 341

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 17 September 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

Thu 6/11

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

Mon 10/11

11:00 a.m.-4:30 p.m.

1 stop4h 30m

C$ 333

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 17/10

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

1 stop4h 14m

Chicago Midway

Mon 20/10

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

1 stop3h 55m

C$ 351

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 14/10

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

1 stop4h 14m

Chicago Midway

Tue 21/10

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

1 stop3h 55m

C$ 356

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 14/10

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

1 stop6h 39m

Chicago Midway

Mon 20/10

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

1 stop3h 55m

C$ 391

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 14/10

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

1 stop6h 39m

Chicago Midway

Thu 12/3

11:00 a.m.-6:45 p.m.

1 stop6h 45m

C$ 393

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 12/10

6:00 a.m.-12:28 p.m.

1 stop7h 28m

Chicago Midway

Tue 21/10

5:04 p.m.-11:48 p.m.

1 stop5h 44m

C$ 398

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 15/10

7:00 a.m.-4:09 p.m.

1 stop10h 09m

Chicago Midway

Fri 24/10

5:04 p.m.-11:48 p.m.

1 stop5h 44m

C$ 398

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 15/10

7:00 a.m.-4:09 p.m.

1 stop10h 09m

Chicago Midway

Thu 23/10

10:35 a.m.-5:34 p.m.

1 stop5h 59m

C$ 398

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 12/10

6:00 a.m.-12:28 p.m.

1 stop7h 28m

Chicago Midway

Sat 25/10

4:23 p.m.-11:48 p.m.

1 stop6h 25m

C$ 398

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 12/10

6:00 a.m.-12:28 p.m.

1 stop7h 28m

Chicago Midway

Fri 24/10

5:04 p.m.-11:48 p.m.

1 stop5h 44m

C$ 398

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/9

Showing 1-10 of 22 results
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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, September 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$ 207). 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 17 September 2025.
See what other customers who have flown with Porter Airlines 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
7.9
Good
365 reviews
Check prices

Entertainment

7.0

Comfort

7.9

Overall

7.9

Crew

8.6

Boarding

8.2

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
7.9
Good
365 reviews
Porter Airlines
7.9
Good
365 reviews
Check prices

Entertainment

7.0

Comfort

7.9

Overall

7.9

Crew

8.6

Boarding

8.2

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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.

  • How long is the flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

    For as low as C$ 333, Porter Airlines can have you in Chicago Midway Airport from Montreal Pierre Elliott Trudeau Intl Airport in 4h 20m. The distance from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport is about 1196 km.

  • What is the cheapest airline to fly 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$ 202 on this airline. Users have found that Porter Airlines is 53% cheaper than the other options available to this destination.

  • 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, September 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$ 207). 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 17 September 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 202AverageC$ 438FlexibilityNo 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?

When you search for this flight from Pierre Elliott Trudeau Intl to Midway, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

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Can Cheapflights find flights from Pierre Elliott Trudeau Intl to Midway with no change fees?

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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