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Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport from C$ 227

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 25/11. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — MDW
26 Nov — 3 Dec1
1 adult
1 adult, Economy, 0 bags

Find flight deals from Pierre Elliott Trudeau Intl to Midway

Enter your travel dates to find the best prices.

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 27 October 2025.

Thu 4/1210:15 a.m.YUL - MDW
1 stop6h 05mPorter Airlines
Sun 7/1211:00 a.m.MDW - YUL
1 stop5h 45mPorter Airlines
Deal found 25/10C$ 368
Tue 9/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Fri 12/1211:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 26/10C$ 371
Sat 22/118:55 a.m.YUL - MDW
1 stop3h 55mPorter Airlines
Sat 29/1112:45 p.m.MDW - YUL
1 stop5h 05mPorter Airlines
Deal found 25/10C$ 381
Mon 24/116:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Sat 29/1112:45 p.m.MDW - YUL
1 stop5h 05mPorter Airlines
Deal found 25/10C$ 386
Sat 22/118:55 a.m.YUL - MDW
1 stop3h 55mPorter Airlines
Wed 26/1111:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 26/10C$ 392
Thu 11/1211:25 a.m.YUL - MDW
1 stop4h 55mPorter Airlines
Thu 18/1211:00 a.m.MDW - YUL
1 stop5h 45mPorter Airlines
Deal found 27/10C$ 393
Thu 20/1111:25 a.m.YUL - MDW
1 stop4h 55mPorter Airlines
Mon 24/114:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 26/10C$ 399
Wed 19/116:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Tue 25/1111:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 26/10C$ 400
Fri 21/1111:25 a.m.YUL - MDW
1 stop4h 55mPorter Airlines
Mon 24/114:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 26/10C$ 403

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 27 October 2025.

Round-trip from

C$ 368

One-way from

C$ 227

Popular in

October

Cheapest in

September

Average price

C$ 627
Porter Airlines
  • Porter Airlines
  • 4/12-7/12
  • 2 total stops
  • 11h 50m total
  • Montreal to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 25/11
  • 1 total stop
  • 4h 20m total
  • Montreal to Chicago
Search Deals
High demand for flights, 3% potential price rise
Search Deals
Cheapest flight prices on average. 4% potential price decrease (C$ 25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 27 October 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 4/12

10:15 a.m.-3:20 p.m.

1 stop6h 05m

Chicago Midway

Sun 7/12

11:00 a.m.-5:45 p.m.

1 stop5h 45m

C$ 368

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 2/3

12:45 p.m.-9:46 p.m.

1 stop10h 01m

Chicago Midway

Mon 9/3

2:00 p.m.-11:39 p.m.

1 stop8h 39m

C$ 385

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 11/12

11:25 a.m.-3:20 p.m.

1 stop4h 55m

Chicago Midway

Thu 18/12

11:00 a.m.-5:45 p.m.

1 stop5h 45m

C$ 393

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 20/11

10:15 a.m.-3:20 p.m.

1 stop6h 05m

Chicago Midway

Mon 24/11

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

1 stop4h 30m

C$ 399

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 21/11

11:25 a.m.-3:20 p.m.

1 stop4h 55m

Chicago Midway

Mon 24/11

4:15 p.m.-10:45 p.m.

1 stop5h 30m

C$ 399

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 11/12

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

1 stop4h 20m

Chicago Midway

Mon 15/12

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

1 stop6h 45m

C$ 416

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 23/11

12:50 p.m.-6:08 p.m.

1 stop6h 18m

Chicago Midway

Wed 26/11

9:34 a.m.-3:55 p.m.

1 stop5h 21m

C$ 423

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 26/11

6:26 p.m.-11:40 p.m.

1 stop6h 14m

Chicago Midway

Mon 1/12

5:34 p.m.-11:59 p.m.

1 stop5h 25m

C$ 423

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 21/11

6:26 p.m.-11:40 p.m.

1 stop6h 14m

Chicago Midway

Tue 25/11

10:47 a.m.-5:21 p.m.

1 stop5h 34m

C$ 423

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 20/11

7:00 a.m.-11:52 a.m.

1 stop5h 52m

Chicago Midway

Mon 24/11

1:47 p.m.-11:42 p.m.

1 stop8h 55m

C$ 423

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/10

Showing 1-10 of 20 results
1
2

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$ 183). Flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport in January is currently the most expensive (average of C$ 420). 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 27 October 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
8.0
Very good
384 reviews
Check prices

Comfort

8.0

Overall

8.0

Entertainment

7.0

Boarding

8.2

Crew

8.6

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
8.0
Very good
384 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Comfort

8.0

Overall

8.0

Entertainment

7.0

Boarding

8.2

Crew

8.6

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$ 368, Porter Airlines can have you in Chicago Midway Airport from Montreal Pierre Elliott Trudeau Intl Airport in 6h 05m. The distance from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport is about 1196 km. Both multi-stop and direct flights can be found to your destination and back.

  • 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$ 199 on this airline. Users have found that Porter Airlines is 54% 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$ 183). Flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport in January is currently the most expensive (average of C$ 420). 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 27 October 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 199AverageC$ 444FlexibilityNo 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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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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