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Cheap flights from Montreal to Chicago Midway Airport from C$ 240

YMQ — MDW
22 Oct — 29 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 17/106:30 a.m. -
1 stop5h 30m
Wed 21/103:20 p.m. -
1 stop4h 52m
Deal found 21/9C$ 398
Thu 15/106:30 a.m. -
1 stop5h 30m
Sun 18/103:20 p.m. -
1 stop4h 52m
Deal found 17/9C$ 401
Fri 16/106:30 a.m. -
1 stop5h 30m
Tue 20/103:20 p.m. -
1 stop4h 52m
Deal found 21/9C$ 406
Tue 13/106:30 a.m. -
1 stop5h 30m
Sat 17/1011:45 a.m. -
1 stop5h 27m
Deal found 20/9C$ 411
Thu 1/106:30 a.m. -
1 stop5h 30m
Sun 4/103:20 p.m. -
1 stop4h 52m
Deal found 17/9C$ 412
Tue 6/106:30 a.m. -
1 stop5h 30m
Sun 11/1011:45 a.m. -
1 stop5h 27m
Deal found 18/9C$ 413
Mon 19/106:30 a.m. -
1 stop5h 30m
Tue 20/103:20 p.m. -
1 stop4h 52m
Deal found 18/9C$ 416
Fri 2/106:30 a.m. -
1 stop5h 30m
Mon 5/1011:45 a.m. -
1 stop5h 27m
Deal found 19/9C$ 418
Sat 10/106:30 a.m. -
1 stop9h 05m
Sun 11/103:20 p.m. -
1 stop4h 52m
Deal found 21/9C$ 425
Thu 15/106:00 a.m. -
1 stop7h 47m
Tue 20/101:27 p.m. -
1 stop8h 58m
Deal found 21/9C$ 427
Tue 20/106:30 a.m. -
1 stop5h 30m
Tue 20/103:20 p.m. -
1 stop4h 52m
Deal found 21/9C$ 433
Fri 16/1010:00 a.m. -
1 stop5h 35m
Mon 19/103:20 p.m. -
1 stop3h 55m
Deal found 19/9C$ 444

Find flight deals from Montreal to Midway

Round-trip from

C$ 398

One-way from

C$ 240

Popular in

July

Cheapest in

April

Average price

C$ 450
Porter Airlines
  • Porter Airlines
  • 17/10-19/10
  • 2 total stops
  • 10h 22m total
  • Montreal to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 23/10-31/12
  • 1 total stop
  • 5h 30m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (C$ 71 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
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

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$ 258

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 25/11

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$ 258

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 4/11

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$ 258

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 6/12

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$ 258

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$ 258

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 27/10

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$ 258

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 6/10

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$ 258

MontrealChicago

YHU Montreal St Hubert - MDW Chicago Midway

YHUMDW

Montreal St Hubert

Thu 22/10

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$ 266

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 15/11

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$ 272

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$ 276

Flights are sorted by cheapest round-trip flights first.

Deals found on 18/9

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
462 reviews
Check prices

Crew

8.6

Entertainment

6.9

Boarding

8.2

Food

7.6

Comfort

8.0

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
462 reviews
Porter Airlines
8.0
Very good
462 reviews
Check prices

Crew

8.6

Entertainment

6.9

Boarding

8.2

Food

7.6

Comfort

8.0

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 5h 35m. The time it takes to get you to your destination can typically vary by up to 2h 16m. 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$ 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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