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Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport from C$ 240

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 16/8. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — MDW
28 Jul — 4 Aug1
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 28 June 2026.

Mon 10/86:30 a.m.
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Mon 17/83:15 p.m.
MDW
-
YUL
1 stop3h 55m
Porter Airlines
Deal found 26/6C$ 403
Fri 24/710:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Tue 28/73:20 p.m.
MDW
-
YUL
1 stop3h 50m
Porter Airlines
Deal found 24/6C$ 407
Thu 16/710:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Sun 19/710:25 a.m.
MDW
-
YUL
1 stop6h 45m
Porter Airlines
Deal found 27/6C$ 409
Tue 14/76:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Tue 14/73:20 p.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 27/6C$ 410
Fri 24/710:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Mon 27/73:20 p.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 24/6C$ 413
Thu 13/86:30 a.m.
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Mon 17/83:15 p.m.
MDW
-
YUL
1 stop3h 55m
Porter Airlines
Deal found 26/6C$ 414
Thu 23/710:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Sun 26/73:20 p.m.
MDW
-
YUL
1 stop3h 50m
Porter Airlines
Deal found 27/6C$ 417
Wed 8/710:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Sun 12/73:20 p.m.
MDW
-
YUL
1 stop3h 50m
Porter Airlines
Deal found 24/6C$ 419
Thu 30/76:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Sat 1/810:20 a.m.
MDW
-
YUL
1 stop6h 50m
Porter Airlines
Deal found 28/6C$ 420
Fri 17/710:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Thu 30/73:20 p.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 26/6C$ 423

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 28 June 2026.

Round-trip from

C$ 403

One-way from

C$ 240

Popular in

October

Cheapest in

May

Average price

C$ 511
Porter Airlines
  • Porter Airlines
  • 10/8-17/8
  • 2 total stops
  • 8h 10m total
  • Montreal to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 16/8
  • 1 total stop
  • 5h 00m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 18% potential increase in price (C$ 152 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 43 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
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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 28 June 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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 28/10

12:45 p.m.-6:37 p.m.

1 stop6h 52m

Chicago Midway

Sat 31/10

9:30 a.m.-3:59 p.m.

1 stop5h 29m

C$ 444

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 27/8

10:35 a.m.-2:35 p.m.

1 stop5h 00m

Chicago Midway

Mon 31/8

3:15 p.m.-8:10 p.m.

1 stop3h 55m

C$ 453
Quickest round-trip

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 24/8

6:30 a.m.-9:45 a.m.

1 stop4h 15m

Chicago Midway

Mon 24/8

3:15 p.m.-8:10 p.m.

1 stop3h 55m

C$ 454

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 20/8

6:30 a.m.-9:45 a.m.

1 stop4h 15m

Chicago Midway

Mon 24/8

3:15 p.m.-8:10 p.m.

1 stop3h 55m

C$ 454

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 6/8

6:30 a.m.-9:45 a.m.

1 stop4h 15m

Chicago Midway

Mon 10/8

3:15 p.m.-8:10 p.m.

1 stop3h 55m

C$ 454

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 20/10

6:00 a.m.-12:33 p.m.

1 stop7h 33m

Chicago Midway

Mon 26/10

6:30 p.m.-11:10 p.m.

1 stop3h 40m

C$ 468

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 26/11

6:00 a.m.-12:33 p.m.

1 stop7h 33m

Chicago Midway

Wed 2/12

9:30 a.m.-3:59 p.m.

1 stop5h 29m

C$ 473

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 10/8

6:30 a.m.-9:45 a.m.

1 stop4h 15m

Chicago Midway

Sat 15/8

10:20 a.m.-6:10 p.m.

1 stop6h 50m

C$ 485

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 8/7

6:00 a.m.-9:13 a.m.

1 stop4h 13m

Chicago Midway

Thu 9/7

1:18 p.m.-11:25 p.m.

1 stop9h 07m

C$ 501

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 4/9

6:00 a.m.-9:17 a.m.

1 stop4h 17m

Chicago Midway

Mon 7/9

9:24 a.m.-4:20 p.m.

1 stop5h 56m

C$ 504

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/6

Showing 1-10 of 22 resultsSorted by cheapest first
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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

How much does it cost to fly round-trip from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

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 28 June 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
8.0
Very good
441 reviews
Check prices

Crew

8.6

Entertainment

6.9

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.5

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.
Porter Airlines
8.0
Very good
441 reviews
Porter Airlines
8.0
Very good
441 reviews
Check prices

Crew

8.6

Entertainment

6.9

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.5

Reviews

1 / 20
6.0
Good

Justin,May 2026

YYZ - MCO

Staff very nice. Seats were uncomfortable. Complimentary snacks leave much to be desired.

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$ 453, Delta can have you in Chicago Midway Airport from Montreal Pierre Elliott Trudeau Intl Airport in 5h. 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$ 208 on this airline. Users have found that Porter Airlines is 55% 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 28 June 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 208AverageC$ 402FlexibilityNo 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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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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