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Cheap flights from Montreal to Chicago Midway Airport from C$ 253

YMQ — MDW
7 Nov — 14 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

Wed 4/116:00 a.m. -
1 stop7h 47m
Tue 17/115:13 p.m. -
1 stop5h 35m
Deal found 6/10C$ 417
Tue 8/127:00 a.m. -
1 stop10h 16m
Thu 10/121:02 p.m. -
1 stop9h 46m
Deal found 5/10C$ 421
Sat 31/102:46 p.m. -
1 stop8h 47m
Sun 1/116:44 p.m. -
1 stop3h 41m
Deal found 7/10C$ 423
Mon 9/116:00 a.m. -
1 stop7h 51m
Mon 16/1112:30 p.m. -
1 stop10h 00m
Deal found 6/10C$ 453
Sat 24/106:00 a.m. -
1 stop7h 47m
Fri 30/1012:49 p.m. -
1 stop10h 05m
Deal found 7/10C$ 457
Thu 29/106:00 a.m. -
1 stop4h 32m
Sun 1/116:44 p.m. -
1 stop3h 41m
Deal found 4/10C$ 468
Sat 31/106:00 a.m. -
1 stop4h 32m
Sun 1/116:44 p.m. -
1 stop3h 41m
Deal found 5/10C$ 471
Thu 5/116:00 a.m. -
1 stop4h 32m
Sun 8/111:27 p.m. -
1 stop8h 58m
Deal found 6/10C$ 474
Sun 15/116:00 a.m. -
1 stop7h 51m
Tue 24/119:30 a.m. -
1 stop5h 28m
Deal found 6/10C$ 478
Mon 9/116:00 a.m. -
1 stop7h 51m
Sun 15/116:00 a.m. -
1 stop10h 27m
Deal found 6/10C$ 480
Wed 11/117:00 a.m. -
1 stop10h 18m
Sun 15/116:00 a.m. -
1 stop10h 27m
Deal found 6/10C$ 481
Thu 29/106:00 a.m. -
1 stop4h 32m
Sun 1/116:44 p.m. -
1 stop3h 41m
Deal found 5/10C$ 483

Find flight deals from Montreal to Midway

Round-trip from

C$ 417

One-way from

C$ 253

Popular in

July

Cheapest in

April

Average price

C$ 515
Delta
  • Delta
  • 4/11-14/11
  • 2 total stops
  • 11h 07m total
  • Montreal to Chicago
Search Deals
Delta
  • Delta
  • 23/11-31/12
  • 1 total stop
  • 5h 40m 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).
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
Quickest round-trip

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$ 253

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 4/11

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$ 253

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 28/10

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$ 253

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$ 253

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 8/11

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$ 283

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 12/12

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$ 283

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 27/10

7:00 a.m.-4:14 p.m.

1 stop10h 14m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 288

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 30/1

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$ 328

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 21/10

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$ 337

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 10/1

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$ 352

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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
467 reviews
Check prices

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.6

Comfort

8.0

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
467 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Entertainment

7.0

Overall

8.0

Boarding

8.2

Crew

8.6

Comfort

8.0

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 4h 46m. The time it takes to get you to your destination can typically vary by up to 2h 24m. 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$ 249, 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$ 249AverageC$ 468FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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