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Cheap flights from Montreal to Chicago Midway Airport from C$ 254

YMQ — MDW
13 Nov — 20 Nov1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Montreal to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Montreal to Midway

Fri 20/116:00 a.m. -
1 stop4h 46m
Sun 29/116:00 a.m. -
1 stop10h 27m
Deal found 9/10C$ 423
Thu 19/117:10 a.m. -
1 stop10h 29m
Mon 23/111:31 p.m. -
1 stop8h 56m
Deal found 12/10C$ 437
Wed 4/116:00 a.m. -
1 stop4h 32m
Sat 7/115:31 p.m. -
1 stop4h 51m
Deal found 13/10C$ 464
Fri 20/117:10 a.m. -
1 stop10h 29m
Tue 24/119:30 a.m. -
1 stop5h 28m
Deal found 11/10C$ 471
Sun 22/117:10 a.m. -
1 stop5h 40m
Fri 27/1112:05 p.m. -
1 stop6h 42m
Deal found 13/10C$ 481
Tue 10/116:00 a.m. -
1 stop4h 46m
Tue 17/115:13 p.m. -
1 stop5h 35m
Deal found 13/10C$ 483
Thu 5/116:00 a.m. -
1 stop4h 32m
Sat 7/119:29 a.m. -
1 stop5h 46m
Deal found 14/10C$ 484
Wed 28/106:00 a.m. -
1 stop4h 32m
Tue 3/111:27 p.m. -
1 stop8h 58m
Deal found 11/10C$ 497
Tue 27/107:07 a.m. -
1 stop10h 14m
Fri 6/116:51 p.m. -
1 stop3h 41m
Deal found 10/10C$ 517
Thu 29/106:00 a.m. -
1 stop7h 47m
Tue 24/116:44 p.m. -
1 stop3h 43m
Deal found 10/10C$ 523
Thu 5/116:00 a.m. -
1 stop4h 32m
Sun 8/119:29 a.m. -
1 stop5h 46m
Deal found 13/10C$ 526
Tue 3/116:00 a.m. -
1 stop4h 32m
Tue 10/115:13 p.m. -
1 stop5h 35m
Deal found 14/10C$ 528

Find flight deals from Montreal to Midway

Round-trip from

C$ 423

One-way from

C$ 254

Popular in

July

Cheapest in

April

Average price

C$ 504
Delta
  • Delta
  • 20/11-27/11
  • 2 total stops
  • 11h 28m total
  • Montreal to Chicago
Search Deals
Delta
  • Delta
  • 12/12-31/12
  • 1 total stop
  • 10h 40m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 78 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2026
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Cheapflights Fare Finder

 
Use the filters below to find and compare flights from Montreal 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

Sat 12/12

7:10 a.m.-4:50 p.m.

1 stop10h 40m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 254

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 18/11

7:00 a.m.-11:59 a.m.

1 stop5h 59m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 261

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 14/2

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

1 stop7h 33m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 261

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 23/11

12:50 p.m.-6:04 p.m.

1 stop6h 14m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 283

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 21/11

2:43 p.m.-10:54 p.m.

1 stop9h 11m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 283

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 7/11

12:50 p.m.-6:00 p.m.

1 stop6h 10m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 283

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 1/12

12:50 p.m.-6:01 p.m.

1 stop6h 11m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 283

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 19/11

6:00 a.m.-12:51 p.m.

1 stop7h 51m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 283

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 26/11

7:00 a.m.-3:15 p.m.

1 stop9h 15m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 283

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 14/11

2:43 p.m.-10:54 p.m.

1 stop9h 11m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 283

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 42 resultsSorted by cheapest first
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Best time to book a flight from Montreal to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Montreal with our price prediction graph.
Estimated round-trip price

Cheapflights Insights

Everything you need to know about your flight from Montreal to Chicago Midway Airport

No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Midway

Read through reviews of airlines operating flights from Montreal to Chicago Midway Airport, such as Porter Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
468 reviews
Check prices

Food

7.6

Overall

8.0

Entertainment

6.9

Comfort

8.0

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Porter Airlines
8.0
Very good
468 reviews
Porter Airlines
8.0
Very good
468 reviews
Check prices

Food

7.6

Overall

8.0

Entertainment

6.9

Comfort

8.0

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Related info for your journey

  • How long is the flight from Montreal to Chicago Midway Airport?

    Airlines like Delta and Porter Airlines fly from Montreal to Chicago Midway Airport in about 5h. The time it takes to get you to your destination can typically vary by up to 5h 16m. Montreal and Chicago Midway Airport are separated by a distance of 1221 km. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Montreal to Chicago Midway Airport round-trip?

    Porter Airlines, at C$ 249, was found to be the cheapest airline from Montreal to Chicago Midway Airport..

  • Can I find deals for flights from Montreal to Midway that include hotel bookings?

    Yes. In addition to deals on Montreal to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Montreal to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Montreal to Midway.

  • Can I find deals for business class flights from Montreal to Midway?

    Yes. Cheapflights offers flight deals from Montreal 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

Browse thousands of different options on Cheapflights for your next trip

Top airline flying from Montreal to Midway

AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 249AverageC$ 468FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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