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Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport from C$ 237

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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — MDW
10 Jan — 17 Jan1
1 adult
1 adult, Economy, 0 bags

Cheap 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 11 December 2025.

Sat 27/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Mon 23/211:00 a.m.MDW - YUL
1 stop6h 45mPorter Airlines
Deal found 10/12C$ 338
Tue 30/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Mon 5/14:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 9/12C$ 401
Wed 31/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Thu 8/111:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 9/12C$ 436
Tue 30/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Sat 10/112:45 p.m.MDW - YUL
1 stop5h 00mPorter Airlines
Deal found 9/12C$ 444
Wed 31/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Wed 7/111:00 a.m.MDW - YUL
1 stop5h 45mPorter Airlines
Deal found 9/12C$ 461
Mon 29/1211:25 a.m.YUL - MDW
1 stop4h 55mPorter Airlines
Mon 5/14:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 9/12C$ 464
Tue 30/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Sun 11/111:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 9/12C$ 482
Tue 30/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Fri 9/111:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 9/12C$ 491
Mon 29/1211:25 a.m.YUL - MDW
1 stop4h 55mPorter Airlines
Sat 10/112:45 p.m.MDW - YUL
1 stop5h 00mPorter Airlines
Deal found 9/12C$ 504

Find 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 11 December 2025.

Round-trip from

C$ 260

One-way from

C$ 237

Popular in

October

Cheapest in

September

Average price

C$ 453
Porter Airlines
  • Porter Airlines
  • 14/2-17/2
  • 2 total stops
  • 10h 40m total
  • Montreal to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 5/1
  • 1 total stop
  • 4h 20m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (C$ 99 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 37 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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 11 December 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

Sat 14/2

8:55 a.m.-11:50 a.m.

1 stop3h 55m

Chicago Midway

Tue 17/2

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

1 stop6h 45m

C$ 260

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 15/2

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

1 stop4h 20m

Chicago Midway

Wed 18/2

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

1 stop4h 30m

C$ 293

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 15/2

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

1 stop4h 20m

Chicago Midway

Thu 19/2

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

1 stop4h 30m

C$ 293

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 17/2

7:00 a.m.-11:59 a.m.

1 stop5h 59m

Chicago Midway

Wed 18/2

1:28 p.m.-11:10 p.m.

1 stop8h 42m

C$ 298

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 21/4

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

1 stop4h 20m

Chicago Midway

Sun 26/4

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

1 stop6h 45m

C$ 363

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 16/4

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

1 stop4h 55m

Chicago Midway

Mon 20/4

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

1 stop5h 45m

C$ 369

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 11/3

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

1 stop4h 20m

Chicago Midway

Wed 25/3

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

1 stop4h 30m

C$ 371

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 17/2

6:00 a.m.-12:46 p.m.

1 stop7h 46m

Chicago Midway

Thu 19/2

6:00 a.m.-4:53 p.m.

1 stop9h 53m

C$ 378

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 5/1

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

1 stop4h 25m

Chicago Midway

Thu 8/1

11:05 a.m.-5:45 p.m.

1 stop5h 40m

C$ 401

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 30/12

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

1 stop4h 20m

Chicago Midway

Thu 8/1

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

1 stop4h 30m

C$ 403

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Showing 1-10 of 23 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$ 181). Flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport in January is currently the most expensive (average of C$ 423). 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 11 December 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
397 reviews
Check prices

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
8.0
Very good
397 reviews
Porter Airlines
8.0
Very good
397 reviews
Check prices

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.0

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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$ 260, Porter Airlines can have you in Chicago Midway Airport from Montreal Pierre Elliott Trudeau Intl Airport in 3h 55m. 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$ 197 on this airline. Users have found that Porter Airlines is 57% 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$ 181). Flying from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport in January is currently the most expensive (average of C$ 423). 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 11 December 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 197AverageC$ 448FlexibilityNo 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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Millions of users choose and trust Cheapflights to book the best flight deals from Pierre Elliott Trudeau Intl to Midway for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

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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