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Cheap flights from Montreal to Chicago Midway Airport from C$ 272

YMQ — MDW
19 Nov — 26 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

Sun 8/116:00 a.m. -
1 stop7h 47m
Wed 11/111:31 p.m. -
1 stop8h 56m
Deal found 17/10C$ 460
Sat 7/1112:50 p.m. -
1 stop6h 10m
Sun 8/119:29 a.m. -
1 stop5h 46m
Deal found 15/10C$ 478
Thu 5/116:00 a.m. -
1 stop4h 32m
Wed 11/111:31 p.m. -
1 stop8h 56m
Deal found 14/10C$ 480
Thu 19/117:10 a.m. -
1 stop10h 29m
Mon 23/111:31 p.m. -
1 stop8h 56m
Deal found 16/10C$ 481
Fri 13/116:00 a.m. -
1 stop4h 46m
Tue 17/116:44 p.m. -
1 stop3h 43m
Deal found 19/10C$ 482
Thu 19/1112:50 p.m. -
1 stop6h 14m
Mon 23/115:29 p.m. -
1 stop5h 01m
Deal found 16/10C$ 495
Sun 8/116:00 a.m. -
1 stop7h 47m
Sun 22/116:44 p.m. -
1 stop3h 43m
Deal found 14/10C$ 520
Fri 6/116:00 a.m. -
1 stop7h 47m
Sun 8/119:29 a.m. -
1 stop5h 46m
Deal found 16/10C$ 522
Tue 3/116:00 a.m. -
1 stop4h 32m
Tue 10/115:13 p.m. -
1 stop5h 35m
Deal found 14/10C$ 523
Sat 14/117:10 a.m. -
1 stop10h 29m
Sun 15/119:30 a.m. -
1 stop5h 28m
Deal found 19/10C$ 525
Wed 4/116:05 a.m. -
1 stop7h 47m
Mon 9/116:49 p.m. -
1 stop3h 43m
Deal found 14/10C$ 526
Fri 13/116:00 a.m. -
1 stop4h 46m
Tue 17/111:31 p.m. -
1 stop8h 56m
Deal found 18/10C$ 530

Find flight deals from Montreal to Midway

Round-trip from

C$ 422

One-way from

C$ 272

Popular in

July

Cheapest in

April

Average price

C$ 495
Delta
  • Delta
  • 3/12-10/12
  • 2 total stops
  • 13h 29m total
  • Montreal to Chicago
Search Deals
KLM
  • KLM
  • 10/11-31/12
  • 1 total stop
  • 5h 59m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 74 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 24/11

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$ 281

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 28/11

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$ 281

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 8/11

7:00 a.m.-11:54 a.m.

1 stop5h 54m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 281

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 23/11

7:10 a.m.-11:50 a.m.

1 stop5h 40m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 281

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$ 281

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 11/11

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$ 282
Quickest round-trip

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 9/11

6:00 a.m.-9:46 a.m.

1 stop4h 46m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 282

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$ 283

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 14/11

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$ 324

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 1/4

7:00 a.m.-11:51 a.m.

1 stop5h 51m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 334

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/10

Showing 1-10 of 41 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

Comfort

8.0

Crew

8.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

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

Comfort

8.0

Crew

8.6

Entertainment

7.0

Boarding

8.2

Overall

8.0

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 9h 15m. The time it takes to get you to your destination can typically vary by up to 6h 35m. Montreal and Chicago Midway Airport are separated by a distance of 1196 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$ 247, 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$ 247AverageC$ 464FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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