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Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport from C$ 142

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 30/3. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — MDW
11 Mar — 18 Mar1
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 9 February 2026.

Sat 25/48:55 a.m.
YUL
-
MDW
1 stop3h 55m
Porter Airlines
Wed 29/411:00 a.m.
MDW
-
YUL
1 stop4h 30m
Porter Airlines
Deal found 6/2C$ 241
Fri 10/46:45 a.m.
YUL
-
MDW
1 stop4h 20m
Porter Airlines
Sun 12/411:00 a.m.
MDW
-
YUL
1 stop6h 45m
Porter Airlines
Deal found 6/2C$ 256
Thu 21/510:35 a.m.
YUL
-
MDW
1 stop7h 15m
Porter Airlines
Sun 24/510:25 a.m.
MDW
-
YUL
1 stop6h 50m
Porter Airlines
Deal found 8/2C$ 257
Fri 22/510:35 a.m.
YUL
-
MDW
1 stop7h 15m
Porter Airlines
Thu 28/510:25 a.m.
MDW
-
YUL
1 stop6h 50m
Porter Airlines
Deal found 6/2C$ 267
Tue 26/51:00 p.m.
YUL
-
MDW
1 stop4h 50m
Porter Airlines
Sun 31/510:25 a.m.
MDW
-
YUL
1 stop6h 50m
Porter Airlines
Deal found 6/2C$ 269
Mon 11/56:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Fri 15/510:25 a.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 6/2C$ 272
Fri 24/46:45 a.m.
YUL
-
MDW
1 stop4h 20m
Porter Airlines
Mon 27/411:00 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 8/2C$ 273
Thu 4/610:35 a.m.
YUL
-
MDW
1 stop7h 15m
Porter Airlines
Sun 7/610:25 a.m.
MDW
-
YUL
1 stop6h 50m
Porter Airlines
Deal found 8/2C$ 275
Wed 27/56:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Tue 2/610:25 a.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 6/2C$ 282
Mon 9/36:50 a.m.
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Wed 11/311:00 a.m.
MDW
-
YUL
1 stop4h 30m
Porter Airlines
Deal found 7/2C$ 294
Sat 23/512:40 p.m.
YUL
-
MDW
1 stop9h 29m
Delta
Thu 28/510:46 a.m.
MDW
-
YUL
1 stop5h 54m
Delta
Deal found 6/2C$ 298

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 9 February 2026.

Round-trip from

C$ 241

One-way from

C$ 142

Popular in

October

Cheapest in

September

Average price

C$ 619
Porter Airlines
  • Porter Airlines
  • 25/4-29/4
  • 2 total stops
  • 8h 25m total
  • Montreal to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 30/3
  • 1 total stop
  • 4h 15m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 65 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 February 2026
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 9 February 2026.
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 7/4

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

1 stop4h 20m

Chicago Midway

Tue 14/4

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

1 stop5h 30m

C$ 282

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 28/5

10:35 a.m.-4:50 p.m.

1 stop7h 15m

Chicago Midway

Sun 31/5

10:25 a.m.-6:15 p.m.

1 stop6h 50m

C$ 282

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 29/5

6:30 a.m.-9:40 a.m.

1 stop4h 10m

Chicago Midway

Sun 31/5

10:25 a.m.-6:15 p.m.

1 stop6h 50m

C$ 282

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 26/5

10:35 a.m.-4:50 p.m.

1 stop7h 15m

Chicago Midway

Fri 29/5

10:25 a.m.-5:15 p.m.

1 stop5h 50m

C$ 282

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 18/4

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

1 stop3h 55m

Chicago Midway

Wed 22/4

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

1 stop5h 30m

C$ 282

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 27/5

1:00 p.m.-4:50 p.m.

1 stop4h 50m

Chicago Midway

Sun 31/5

10:25 a.m.-6:15 p.m.

1 stop6h 50m

C$ 282

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 27/5

6:30 a.m.-9:40 a.m.

1 stop4h 10m

Chicago Midway

Tue 2/6

10:25 a.m.-5:15 p.m.

1 stop5h 50m

C$ 282

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 16/4

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

1 stop4h 20m

Chicago Midway

Tue 21/4

11:00 a.m.-6:15 p.m.

1 stop6h 15m

C$ 282

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 7/4

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

1 stop4h 20m

Chicago Midway

Sun 12/4

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

1 stop5h 30m

C$ 282

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 16/4

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

1 stop4h 20m

Chicago Midway

Wed 22/4

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

1 stop5h 30m

C$ 282

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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.

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 9 February 2026.
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
414 reviews
Check prices

Overall

7.9

Entertainment

6.9

Comfort

7.9

Food

7.5

Boarding

8.2

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Milad,Feb 2026

LIR - YYZ

Not helpful staff at Liberia airport at the check-in counter. Extremely poor skill people and not willing to help the passenger.
Porter Airlines
7.9
Good
414 reviews
Porter Airlines
7.9
Good
414 reviews
Check prices

Overall

7.9

Entertainment

6.9

Comfort

7.9

Food

7.5

Boarding

8.2

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Milad,Feb 2026

LIR - YYZ

Not helpful staff at Liberia airport at the check-in counter. Extremely poor skill people and not willing to help the passenger.

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$ 282, 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$ 187 on this airline. Users have found that Porter Airlines is 61% 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.

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 9 February 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 187AverageC$ 377FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

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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.

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.

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