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Cheap flights from Montreal to Chicago Midway Airport from C$ 266

YMQ — MDW
29 Oct — 5 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 16/106:30 a.m. -
1 stop5h 30m
Sun 18/103:20 p.m. -
1 stop4h 52m
Deal found 25/9C$ 435
Thu 22/106:30 a.m. -
1 stop5h 30m
Sat 24/1011:45 a.m. -
1 stop5h 27m
Deal found 28/9C$ 436
Fri 16/106:30 a.m. -
1 stop5h 30m
Tue 20/103:20 p.m. -
1 stop4h 52m
Deal found 25/9C$ 439
Tue 13/106:30 a.m. -
1 stop5h 30m
Mon 19/103:20 p.m. -
1 stop4h 52m
Deal found 27/9C$ 443
Tue 13/106:30 a.m. -
1 stop5h 30m
Tue 20/1011:45 a.m. -
1 stop5h 27m
Deal found 27/9C$ 445
Wed 14/106:30 a.m. -
1 stop5h 30m
Fri 16/103:20 p.m. -
1 stop4h 52m
Deal found 25/9C$ 446
Tue 27/106:00 a.m. -
1 stop7h 47m
Sat 31/106:44 p.m. -
1 stop3h 41m
Deal found 29/9C$ 449
Wed 21/109:00 a.m. -
1 stop6h 35m
Thu 22/103:20 p.m. -
1 stop4h 52m
Deal found 28/9C$ 453
Sat 17/106:30 a.m. -
1 stop5h 30m
Wed 21/103:20 p.m. -
1 stop4h 52m
Deal found 29/9C$ 456
Fri 16/1010:00 a.m. -
1 stop5h 35m
Sun 18/103:20 p.m. -
1 stop3h 55m
Deal found 25/9C$ 503
Thu 15/1010:00 a.m. -
1 stop5h 35m
Tue 20/103:20 p.m. -
1 stop3h 55m
Deal found 24/9C$ 510
Wed 14/108:25 a.m. -
1 stop7h 10m
Tue 20/103:20 p.m. -
1 stop3h 55m
Deal found 24/9C$ 518

Find flight deals from Montreal to Midway

Round-trip from

C$ 435

One-way from

C$ 266

Popular in

July

Cheapest in

April

Average price

C$ 455
Porter Airlines
  • Porter Airlines
  • 16/10-18/10
  • 2 total stops
  • 10h 22m total
  • Montreal to Chicago
Search Deals
Delta
  • Delta
  • 20/10-31/12
  • 1 total stop
  • 4h 32m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 73 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 September 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
Quickest round-trip

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 20/10

6:00 a.m.-9:32 a.m.

1 stop4h 32m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 266

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 14/10

6:00 a.m.-9:32 a.m.

1 stop4h 32m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 266

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 21/10

9:00 a.m.-2:35 p.m.

1 stop6h 35m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 275

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 10/11

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 12/11

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

Sat 14/11

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$ 283

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 5/11

6:00 a.m.-9:32 a.m.

1 stop4h 32m

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

Mon 11/1

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$ 290

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 15/10

6:00 a.m.-9:32 a.m.

1 stop4h 32m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 292

MontrealChicago

YHU MET - Montreal Metropolitan - MDW Chicago Midway

YHUMDW

MET - Montreal Metropolitan

Sat 24/10

8:25 a.m.-2:35 p.m.

1 stop7h 10m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 295

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/9

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
465 reviews
Check prices

Crew

8.6

Entertainment

7.0

Comfort

8.0

Food

7.6

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
465 reviews
Porter Airlines
8.0
Very good
465 reviews
Check prices

Crew

8.6

Entertainment

7.0

Comfort

8.0

Food

7.6

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 4h 32m. The time it takes to get you to your destination can typically vary by up to 1h 03m. 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$ 248, 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$ 248AverageC$ 463FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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