Find flights
When to book
Airlines
FAQs

Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport from C$ 189

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 13/9. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — MDW
20 Aug — 27 Aug1
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 August 2025.

Round-trip from

C$ 296

One-way from

C$ 189

Popular in

October

Cheapest in

September

Average price

C$ 380
Delta
  • Delta
  • 16/9-27/9
  • 2 total stops
  • 14h 23m total
  • Montreal to Chicago
Search Deals
Delta
  • Delta
  • 13/9
  • 1 total stop
  • 9h 26m 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$ 24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

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 August 2025.

Tue 16/97:00 a.m.YUL - MDW
1 stop5h 48mDelta
Sat 27/91:43 p.m.MDW - YUL
1 stop8h 35mDelta
Deal found 13/8C$ 296
Mon 10/116:00 a.m.YUL - MDW
1 stop7h 32mDelta
Mon 17/111:05 p.m.MDW - YUL
1 stop9h 48mDelta
Deal found 14/8C$ 324
Fri 5/91:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Mon 8/95:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Deal found 13/8C$ 329
Wed 10/91:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Wed 17/95:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Deal found 13/8C$ 331
Wed 3/91:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Sun 7/99:35 a.m.MDW - YUL
1 stop5h 25mPorter Airlines
Deal found 13/8C$ 332
Fri 12/910:45 a.m.YUL - MDW
1 stop6h 39mPorter Airlines
Tue 16/95:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Deal found 13/8C$ 334
Fri 12/91:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Sun 14/95:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Deal found 13/8C$ 335
Fri 12/91:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Mon 15/95:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Deal found 13/8C$ 338
Thu 11/910:45 a.m.YUL - MDW
1 stop6h 39mPorter Airlines
Thu 18/99:35 a.m.MDW - YUL
1 stop5h 25mPorter Airlines
Deal found 14/8C$ 341
Thu 18/91:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Sun 21/95:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Deal found 14/8C$ 345
Wed 15/1010:45 a.m.YUL - MDW
1 stop6h 39mPorter Airlines
Sun 19/105:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Deal found 13/8C$ 349

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 August 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

Tue 16/9

7:00 a.m.-11:48 a.m.

1 stop5h 48m

Chicago Midway

Sat 27/9

1:43 p.m.-11:18 p.m.

1 stop8h 35m

C$ 296

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 27/9

10:57 a.m.-5:35 p.m.

1 stop7h 38m

Chicago Midway

Sat 4/10

1:43 p.m.-11:18 p.m.

1 stop8h 35m

C$ 296

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 10/11

6:00 a.m.-12:32 p.m.

1 stop7h 32m

Chicago Midway

Mon 17/11

6:00 a.m.-5:04 p.m.

1 stop10h 04m

C$ 324

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 5/9

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

1 stop4h 14m

Chicago Midway

Mon 8/9

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

1 stop3h 55m

C$ 329

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 12/9

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

1 stop6h 39m

Chicago Midway

Sun 14/9

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

1 stop3h 55m

C$ 329

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 26/9

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

1 stop6h 39m

Chicago Midway

Fri 3/10

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

1 stop3h 55m

C$ 329

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 10/9

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

1 stop4h 14m

Chicago Midway

Wed 17/9

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

1 stop3h 55m

C$ 331

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 3/10

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

1 stop6h 39m

Chicago Midway

Sun 5/10

9:35 a.m.-4:00 p.m.

1 stop5h 25m

C$ 331

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 18/9

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

1 stop6h 39m

Chicago Midway

Mon 22/9

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

1 stop3h 55m

C$ 331

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 19/9

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

1 stop6h 39m

Chicago Midway

Sun 21/9

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

1 stop3h 55m

C$ 331

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/8

Showing 1-10 of 21 results
1
2
3

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$ 233). 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 15 August 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
332 reviews
Check prices

Comfort

8.0

Entertainment

7.0

Crew

8.7

Food

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
332 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Comfort

8.0

Entertainment

7.0

Crew

8.7

Food

7.6

Boarding

8.2

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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 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 52% 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, 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$ 233). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 August 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 202AverageC$ 440FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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.

Why should you use Cheapflights to find cheap flight tickets from Pierre Elliott Trudeau Intl to Midway?

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.