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Cheap flights from Montreal to Chicago Midway Airport from C$ 251

YMQ — MDW
12 Nov — 19 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

Sat 31/102:46 p.m. -
1 stop8h 47m
Sun 1/116:44 p.m. -
1 stop3h 41m
Deal found 8/10C$ 424
Sun 13/126:00 a.m. -
1 stop4h 37m
Wed 16/1212:39 p.m. -
1 stop10h 02m
Deal found 9/10C$ 434
Tue 10/117:10 a.m. -
1 stop5h 40m
Tue 17/115:29 p.m. -
1 stop5h 01m
Deal found 12/10C$ 438
Thu 19/116:00 a.m. -
1 stop7h 51m
Sun 22/116:44 p.m. -
1 stop3h 43m
Deal found 9/10C$ 439
Thu 19/117:10 a.m. -
1 stop10h 29m
Sun 22/116:44 p.m. -
1 stop3h 43m
Deal found 8/10C$ 454
Tue 27/107:00 a.m. -
1 stop10h 14m
Fri 30/1010:59 a.m. -
1 stop5h 39m
Deal found 7/10C$ 458
Fri 20/117:10 a.m. -
1 stop10h 29m
Tue 24/119:30 a.m. -
1 stop5h 28m
Deal found 11/10C$ 472
Thu 12/116:00 a.m. -
1 stop4h 46m
Mon 23/116:44 p.m. -
1 stop3h 43m
Deal found 11/10C$ 484
Tue 24/116:00 a.m. -
1 stop4h 46m
Sun 29/116:44 p.m. -
1 stop3h 43m
Deal found 10/10C$ 485
Sun 1/116:00 a.m. -
1 stop7h 47m
Tue 10/111:05 p.m. -
1 stop9h 43m
Deal found 9/10C$ 496
Wed 28/106:00 a.m. -
1 stop4h 32m
Tue 3/111:27 p.m. -
1 stop8h 58m
Deal found 11/10C$ 498
Thu 22/107:00 a.m. -
1 stop5h 54m
Sat 24/105:31 p.m. -
1 stop4h 51m
Deal found 8/10C$ 516

Find flight deals from Montreal to Midway

Round-trip from

C$ 424

One-way from

C$ 251

Popular in

July

Cheapest in

April

Average price

C$ 505
Delta
  • Delta
  • 31/10-1/11
  • 2 total stops
  • 11h 28m total
  • Montreal to Chicago
Search Deals
KLM
  • KLM
  • 31/10-31/12
  • 1 total stop
  • 8h 47m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 79 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 17 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
Quickest round-trip

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 12/11

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$ 254

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 12/12

7:10 a.m.-4:50 p.m.

1 stop10h 40m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 254

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 28/11

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$ 261

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$ 261

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 20/11

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$ 274

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 14/11

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$ 284

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 13/11

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$ 284

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 1/12

12:50 p.m.-6:01 p.m.

1 stop6h 11m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 284

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 26/11

7:00 a.m.-3:15 p.m.

1 stop9h 15m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 284

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$ 284

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 42 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

Overall

8.0

Entertainment

7.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.6

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

Overall

8.0

Entertainment

7.0

Comfort

8.0

Boarding

8.2

Crew

8.6

Food

7.6

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 5h. The time it takes to get you to your destination can typically vary by up to 2h 51m. Montreal and Chicago Midway Airport are separated by a distance of 1221 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$ 250, 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$ 250AverageC$ 469FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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