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Cheap flights from Montreal to Chicago Midway Airport from C$ 228

YMQ — MDW
7 Oct — 14 Oct1
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 3/106:30 a.m. -
1 stop5h 30m
Sat 10/1011:45 a.m. -
1 stop5h 27m
Deal found 3/9C$ 388
Wed 23/96:30 a.m. -
1 stop5h 30m
Sat 26/911:45 a.m. -
1 stop5h 27m
Deal found 4/9C$ 391
Wed 14/106:30 a.m. -
1 stop5h 30m
Mon 19/1011:45 a.m. -
1 stop5h 27m
Deal found 4/9C$ 393
Fri 25/99:00 a.m. -
1 stop6h 35m
Sun 27/911:45 a.m. -
1 stop5h 27m
Deal found 4/9C$ 394
Sat 26/96:30 a.m. -
1 stop5h 30m
Sun 27/911:45 a.m. -
1 stop5h 27m
Deal found 5/9C$ 395
Thu 22/106:30 a.m. -
1 stop5h 30m
Sat 24/1011:45 a.m. -
1 stop5h 27m
Deal found 7/9C$ 397
Sun 11/1010:35 a.m. -
1 stop5h 00m
Sat 17/1011:45 a.m. -
1 stop5h 27m
Deal found 4/9C$ 398
Thu 24/96:30 a.m. -
1 stop5h 30m
Sun 27/911:45 a.m. -
1 stop5h 27m
Deal found 3/9C$ 401
Thu 24/99:00 a.m. -
1 stop6h 35m
Tue 29/911:45 a.m. -
1 stop5h 27m
Deal found 5/9C$ 402
Sat 19/96:30 a.m. -
1 stop5h 30m
Mon 21/93:20 p.m. -
1 stop4h 52m
Deal found 2/9C$ 406

Find flight deals from Montreal to Midway

Round-trip from

C$ 388

One-way from

C$ 228

Popular in

July

Cheapest in

April

Average price

C$ 424
Porter Airlines
  • Porter Airlines
  • 3/10-10/10
  • 2 total stops
  • 10h 57m total
  • Montreal to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 7/10-31/12
  • 1 total stop
  • 5h 30m 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 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

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 20/10

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$ 235

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 17/11

6:00 a.m.-9:42 a.m.

1 stop4h 42m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 249

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 17/2

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$ 260
Quickest round-trip

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 6/12

6:00 a.m.-9:37 a.m.

1 stop4h 37m

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

Fri 23/10

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$ 268

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 23/9

6:30 a.m.-11:00 a.m.

1 stop5h 30m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 301

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$ 318

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 30/10

6:00 a.m.-12:47 p.m.

1 stop7h 47m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 344

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 9/10

6:45 a.m.-11:43 p.m.

3 stops41h 58m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 366

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 19/9

6:30 a.m.-11:00 a.m.

1 stop5h 30m

Chicago Midway

Mon 21/9

3:20 p.m.-9:12 p.m.

1 stop4h 52m

C$ 406

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/9

Showing 1-10 of 24 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
458 reviews
Check prices

Boarding

8.2

Food

7.6

Comfort

8.0

Crew

8.6

Entertainment

6.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Porter Airlines
8.0
Very good
458 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Boarding

8.2

Food

7.6

Comfort

8.0

Crew

8.6

Entertainment

6.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

Related info for your journey

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

    Airlines like Porter Airlines and Delta fly from Montreal to Chicago Midway Airport in about 5h 30m. The time it takes to get you to your destination can typically vary by up to 2h 17m. 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$ 242, 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$ 242AverageC$ 406FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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Need flexible booking options for your flight to Midway from Montreal? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

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Yes, Cheapflights offers price alerts on Montreal to Midway flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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