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Cheap flights from Montreal to Chicago Midway Airport from C$ 258

YMQ — MDW
24 Nov — 1 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

Sat 19/1212:42 p.m. -
1 stop10h 40m
Mon 4/112:30 p.m. -
1 stop10h 05m
Deal found 21/10C$ 420
Wed 25/116:00 a.m. -
1 stop4h 46m
Sun 29/116:00 a.m. -
1 stop10h 27m
Deal found 23/10C$ 427
Tue 10/1112:50 p.m. -
1 stop6h 14m
Mon 16/116:44 p.m. -
1 stop3h 43m
Deal found 21/10C$ 431
Tue 10/1112:50 p.m. -
1 stop6h 14m
Sat 14/1112:30 p.m. -
1 stop10h 00m
Deal found 23/10C$ 454
Sun 20/127:00 a.m. -
1 stop10h 19m
Mon 4/112:30 p.m. -
1 stop10h 05m
Deal found 21/10C$ 464
Thu 12/116:00 a.m. -
1 stop4h 46m
Sun 22/116:00 a.m. -
1 stop10h 27m
Deal found 21/10C$ 468
Sat 14/117:00 a.m. -
1 stop9h 12m
Sun 15/119:30 a.m. -
1 stop5h 28m
Deal found 20/10C$ 475
Thu 12/116:00 a.m. -
1 stop4h 46m
Mon 16/111:31 p.m. -
1 stop8h 56m
Deal found 23/10C$ 478
Thu 19/116:00 a.m. -
1 stop7h 51m
Mon 23/111:31 p.m. -
1 stop8h 56m
Deal found 25/10C$ 482
Thu 10/127:00 a.m. -
1 stop10h 16m
Sun 13/126:41 p.m. -
1 stop3h 52m
Deal found 23/10C$ 490
Sat 14/117:10 a.m. -
1 stop10h 29m
Sun 15/119:30 a.m. -
1 stop5h 28m
Deal found 20/10C$ 499

Find flight deals from Montreal to Midway

Round-trip from

C$ 420

One-way from

C$ 258

Popular in

July

Cheapest in

April

Average price

C$ 489
Delta
  • Delta
  • 19/12-4/1
  • 2 total stops
  • 20h 45m total
  • Montreal to Chicago
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WestJet
  • WestJet
  • 14/12-31/12
  • 1 total stop
  • 10h 16m 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).
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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
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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

Mon 30/11

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$ 277

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$ 293
Quickest round-trip

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 3/11

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$ 302

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 15/12

9:45 a.m.-11:33 a.m.

3 stops26h 48m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 333

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 22/12

12:42 p.m.-10:22 p.m.

1 stop10h 40m

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

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$ 335

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 9/2

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$ 337

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 9/2

6:45 a.m.-11:46 p.m.

3 stops18h 01m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 371

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 15/11

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$ 375

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 30/10

7:00 a.m.-11:47 a.m.

1 stop5h 47m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 392

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/10

Showing 1-10 of 22 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
467 reviews
Check prices

Boarding

8.2

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.6

Entertainment

6.9

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

Boarding

8.2

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.6

Entertainment

6.9

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 33m. 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$ 245, 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$ 245AverageC$ 458FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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