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Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport from C$ 224

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 11/6. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — MDW
11 Jun — 18 Jun1
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 12 May 2026.

Thu 11/610:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Sun 14/610:15 a.m.
MDW
-
YUL
1 stop6h 00m
Porter Airlines
Deal found 7/5C$ 366
Thu 11/610:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Mon 15/63:20 p.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 11/5C$ 386
Thu 25/610:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Mon 20/710:25 a.m.
MDW
-
YUL
1 stop6h 45m
Porter Airlines
Deal found 9/5C$ 388
Thu 25/610:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Tue 7/73:20 p.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 7/5C$ 391
Thu 25/610:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Sun 28/610:25 a.m.
MDW
-
YUL
1 stop6h 45m
Porter Airlines
Deal found 9/5C$ 392
Thu 4/610:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Sun 7/610:15 a.m.
MDW
-
YUL
1 stop7h 00m
Porter Airlines
Deal found 7/5C$ 409
Thu 23/710:35 a.m.
YUL
-
MDW
1 stop5h 00m
Porter Airlines
Tue 28/73:20 p.m.
MDW
-
YUL
1 stop3h 50m
Porter Airlines
Deal found 11/5C$ 410

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 12 May 2026.

Round-trip from

C$ 368

One-way from

C$ 224

Popular in

October

Cheapest in

September

Average price

C$ 362
Porter Airlines
  • Porter Airlines
  • 11/6-14/6
  • 2 total stops
  • 11h 00m total
  • Montreal to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 11/6
  • 1 total stop
  • 5h 00m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 121 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease (C$ 41 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 12 May 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 17/6

6:30 a.m.-9:35 a.m.

1 stop4h 05m

Chicago Midway

Sat 20/6

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

1 stop6h 45m

C$ 423

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 9/6

7:00 a.m.-1:09 p.m.

1 stop7h 09m

Chicago Midway

Tue 16/6

5:11 p.m.-11:55 p.m.

1 stop5h 44m

C$ 429

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 28/5

7:10 a.m.-1:19 p.m.

1 stop7h 09m

Chicago Midway

Sun 31/5

6:23 a.m.-5:43 p.m.

1 stop10h 20m

C$ 429

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 28/5

6:00 a.m.-8:43 a.m.

1 stop3h 43m

Chicago Midway

Fri 29/5

1:59 p.m.-11:41 p.m.

1 stop8h 42m

C$ 429

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 24/5

12:49 p.m.-6:33 p.m.

1 stop6h 44m

Chicago Midway

Tue 26/5

1:59 p.m.-11:41 p.m.

1 stop8h 42m

C$ 431

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 6/6

6:00 a.m.-12:42 p.m.

1 stop7h 42m

Chicago Midway

Thu 11/6

5:11 p.m.-11:55 p.m.

1 stop5h 44m

C$ 431
Quickest round-trip

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 8/6

6:00 a.m.-9:14 a.m.

1 stop4h 14m

Chicago Midway

Sat 13/6

6:35 p.m.-11:28 p.m.

1 stop3h 53m

C$ 431

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 6/6

12:40 p.m.-9:09 p.m.

1 stop9h 29m

Chicago Midway

Tue 9/6

1:26 p.m.-11:28 p.m.

1 stop9h 02m

C$ 431

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 22/5

12:52 p.m.-6:33 p.m.

1 stop6h 41m

Chicago Midway

Sun 24/5

1:59 p.m.-11:41 p.m.

1 stop8h 42m

C$ 431
Cheapest one-way
Quickest one-way

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 2/6

6:00 a.m.-8:43 a.m.

1 stop3h 43m

C$ 256

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 20 resultsSorted by cheapest first
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

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 12 May 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
436 reviews
Check prices

Comfort

8.0

Food

7.6

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
436 reviews
Porter Airlines
8.0
Very good
436 reviews
Check prices

Comfort

8.0

Food

7.6

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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$ 423, Porter Airlines can have you in Chicago Midway Airport from Montreal Pierre Elliott Trudeau Intl Airport in 4h 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$ 179 on this airline. Users have found that Porter Airlines is 59% 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 12 May 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 179AverageC$ 377FlexibilityNo 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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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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