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Cheap flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport from C$ 228

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 25/8. Fares are subject to change and may not be available on all flights or dates of travel.
YUL — MDW
11 Sep — 18 Sep1
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 August 2026.

Wed 16/96:30 a.m. -
1 stop5h 30m
Wed 16/93:20 p.m. -
1 stop4h 52m
Deal found 9/8C$ 380
Fri 28/86:30 a.m. -
1 stop4h 15m
Sun 30/810:20 a.m. -
1 stop6h 50m
Deal found 7/8C$ 383
Thu 15/106:30 a.m. -
1 stop5h 30m
Thu 22/103:20 p.m. -
1 stop4h 52m
Deal found 11/8C$ 386
Wed 2/912:47 p.m. -
1 stop5h 12m
Sat 17/101:27 p.m. -
1 stop8h 58m
Deal found 10/8C$ 387
Thu 24/96:30 a.m. -
1 stop5h 30m
Sun 27/911:45 a.m. -
1 stop5h 27m
Deal found 11/8C$ 389
Tue 15/99:00 a.m. -
1 stop6h 35m
Thu 17/93:20 p.m. -
1 stop4h 52m
Deal found 10/8C$ 390
Fri 18/99:00 a.m. -
1 stop6h 35m
Wed 23/911:45 a.m. -
1 stop5h 27m
Deal found 8/8C$ 391
Thu 10/96:30 a.m. -
1 stop5h 30m
Sun 13/911:45 a.m. -
1 stop5h 27m
Deal found 10/8C$ 393
Fri 11/99:00 a.m. -
1 stop6h 35m
Sun 13/911:45 a.m. -
1 stop5h 27m
Deal found 11/8C$ 394
Wed 18/1112:50 p.m. -
1 stop6h 14m
Sat 21/1112:30 p.m. -
1 stop10h 00m
Deal found 7/8C$ 396
Fri 25/99:00 a.m. -
1 stop6h 35m
Mon 28/911:45 a.m. -
1 stop5h 27m
Deal found 11/8C$ 397
Sat 5/910:20 a.m. -
1 stop5h 15m
Fri 11/93:20 p.m. -
1 stop4h 52m
Deal found 10/8C$ 398

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 August 2026.

Round-trip from

C$ 380

One-way from

C$ 228

Popular in

October

Cheapest in

May

Average price

C$ 439
Porter Airlines
  • Porter Airlines
  • 16/9-16/9
  • 2 total stops
  • 10h 22m total
  • Montreal to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 25/8
  • 1 total stop
  • 4h 15m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (C$ 193 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease (C$ 61 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 August 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 Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 2/9

12:47 p.m.-4:59 p.m.

1 stop5h 12m

Chicago Midway

Tue 20/10

12:45 p.m.-11:59 p.m.

1 stop10h 14m

C$ 387

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 5/9

7:00 a.m.-3:44 p.m.

1 stop9h 44m

Chicago Midway

Wed 21/10

1:27 p.m.-11:25 p.m.

1 stop8h 58m

C$ 387

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 2/9

7:00 a.m.-3:44 p.m.

1 stop9h 44m

Chicago Midway

Sat 5/9

4:52 p.m.-11:40 p.m.

1 stop5h 48m

C$ 396

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 5/9

2:46 p.m.-10:36 p.m.

1 stop8h 50m

Chicago Midway

Sat 19/9

6:40 p.m.-11:27 p.m.

1 stop3h 47m

C$ 396

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 3/2

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

1 stop6h 52m

Chicago Midway

Sat 6/2

5:25 p.m.-11:51 p.m.

1 stop5h 26m

C$ 397

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 29/8

12:47 p.m.-6:33 p.m.

1 stop6h 46m

Chicago Midway

Wed 2/9

4:39 p.m.-11:52 p.m.

1 stop6h 13m

C$ 407

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 21/10

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

1 stop4h 17m

Chicago Midway

Mon 26/10

9:29 a.m.-4:15 p.m.

1 stop5h 46m

C$ 412
Quickest round-trip

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 18/11

6:00 a.m.-9:42 a.m.

1 stop4h 42m

Chicago Midway

Mon 23/11

6:44 p.m.-11:26 p.m.

1 stop3h 42m

C$ 419

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 3/2

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

1 stop6h 52m

Chicago Midway

Sun 7/2

5:59 p.m.-11:10 p.m.

1 stop4h 11m

C$ 419

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 19/11

6:00 a.m.-9:42 a.m.

1 stop4h 42m

Chicago Midway

Sat 21/11

12:30 p.m.-11:30 p.m.

1 stop10h 00m

C$ 419

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/8

Showing 1-10 of 23 resultsSorted by cheapest first
1
2
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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 12 August 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
456 reviews
Check prices

Entertainment

6.9

Overall

8.0

Food

7.5

Crew

8.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Porter Airlines
8.0
Very good
456 reviews
Porter Airlines
8.0
Very good
456 reviews
Check prices

Entertainment

6.9

Overall

8.0

Food

7.5

Crew

8.6

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

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$ 387, Delta can have you in Chicago Midway Airport from Montreal Pierre Elliott Trudeau Intl Airport in 9h 44m. 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$ 244 on this airline. Users have found that Porter Airlines is 49% 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 August 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 244AverageC$ 436FlexibilityNo 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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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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