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Cheap flights from Montreal to Chicago Midway Airport from C$ 256

YMQ — MDW
29 Nov — 6 Dec1
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

Thu 12/1112:50 p.m. -
1 stop6h 14m
Mon 16/111:05 p.m. -
1 stop9h 43m
Deal found 26/10C$ 420
Thu 3/126:00 a.m. -
1 stop4h 37m
Sun 6/126:41 p.m. -
1 stop3h 52m
Deal found 28/10C$ 451
Thu 19/116:00 a.m. -
1 stop4h 46m
Mon 23/111:31 p.m. -
1 stop8h 56m
Deal found 25/10C$ 459
Wed 11/117:10 a.m. -
1 stop5h 40m
Thu 12/111:05 p.m. -
1 stop9h 43m
Deal found 28/10C$ 468
Fri 20/116:00 a.m. -
1 stop7h 51m
Tue 24/111:31 p.m. -
1 stop8h 56m
Deal found 28/10C$ 469
Mon 16/116:00 a.m. -
1 stop7h 51m
Thu 19/116:00 a.m. -
1 stop10h 27m
Deal found 26/10C$ 471
Fri 20/116:00 a.m. -
1 stop7h 51m
Mon 23/115:29 p.m. -
1 stop5h 01m
Deal found 30/10C$ 478
Thu 19/117:00 a.m. -
1 stop5h 59m
Mon 23/111:31 p.m. -
1 stop8h 56m
Deal found 26/10C$ 480
Wed 18/117:10 a.m. -
1 stop5h 40m
Tue 24/1112:30 p.m. -
1 stop10h 00m
Deal found 29/10C$ 490

Find flight deals from Montreal to Midway

Round-trip from

C$ 420

One-way from

C$ 256

Popular in

July

Cheapest in

April

Average price

C$ 487
Delta
  • Delta
  • 12/11-16/11
  • 2 total stops
  • 15h 57m total
  • Montreal to Chicago
Search Deals
Delta
  • Delta
  • 27/11-31/12
  • 1 total stop
  • 6h 25m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 76 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2026
Search Deals

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

Tue 15/12

6:00 a.m.-1:01 p.m.

1 stop8h 01m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 276

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 14/12

7:00 a.m.-4:16 p.m.

1 stop10h 16m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 286

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 16/11

7:00 a.m.-4:18 p.m.

1 stop10h 18m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 286

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 4/1

6:00 a.m.-1:17 p.m.

1 stop8h 17m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 323

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 22/4

12:45 p.m.-10:10 p.m.

1 stop10h 25m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 325

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 21/2

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$ 335

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 14/12

4:40 p.m.-11:33 a.m.

3 stops19h 53m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 360

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 19/4

7:00 a.m.-4:25 p.m.

1 stop10h 25m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 364

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 9/11

7:10 a.m.-4:39 p.m.

1 stop10h 29m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 390
Quickest round-trip

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 4/11

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$ 420

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/10

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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
467 reviews
Check prices

Food

7.6

Overall

8.0

Crew

8.6

Entertainment

6.9

Comfort

8.0

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
467 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Food

7.6

Overall

8.0

Crew

8.6

Entertainment

6.9

Comfort

8.0

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 fly from Montreal to Chicago Midway Airport in about 7h 51m. The time it takes to get you to your destination can typically vary by up to . Montreal and Chicago Midway Airport are separated by a distance of 1196 km.

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

    Porter Airlines, at C$ 244, 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$ 244AverageC$ 457FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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