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Cheap flights from Montreal to Chicago Midway Airport from C$ 269

YMQ — MDW
12 Dec — 19 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

Fri 4/126:00 a.m. -
1 stop4h 37m
Sat 5/121:41 p.m. -
1 stop8h 52m
Deal found 11/11C$ 454
Thu 26/116:00 a.m. -
1 stop6h 25m
Wed 2/1212:39 p.m. -
1 stop10h 02m
Deal found 11/11C$ 455
Thu 26/116:00 a.m. -
1 stop6h 25m
Sun 29/116:00 a.m. -
1 stop10h 27m
Deal found 10/11C$ 457
Mon 7/127:00 a.m. -
1 stop10h 16m
Fri 11/125:30 p.m. -
1 stop5h 11m
Deal found 11/11C$ 471
Thu 26/116:00 a.m. -
1 stop6h 25m
Sun 29/116:44 p.m. -
1 stop3h 43m
Deal found 11/11C$ 472
Fri 4/126:00 a.m. -
1 stop4h 37m
Sun 13/126:00 a.m. -
1 stop10h 33m
Deal found 8/11C$ 485
Tue 8/126:00 a.m. -
1 stop4h 37m
Wed 16/129:37 a.m. -
1 stop5h 22m
Deal found 7/11C$ 486
Fri 27/117:00 a.m. -
1 stop9h 15m
Sat 28/116:44 p.m. -
1 stop3h 43m
Deal found 11/11C$ 491
Fri 4/126:04 a.m. -
1 stop4h 37m
Mon 7/125:34 p.m. -
1 stop5h 11m
Deal found 11/11C$ 502
Fri 4/126:04 a.m. -
1 stop4h 37m
Sun 6/126:45 p.m. -
1 stop3h 52m
Deal found 10/11C$ 504
Fri 4/126:00 a.m. -
1 stop4h 37m
Thu 10/1212:39 p.m. -
1 stop10h 02m
Deal found 11/11C$ 523

Find flight deals from Montreal to Midway

Round-trip from

C$ 454

One-way from

C$ 269

Popular in

July

Cheapest in

April

Average price

C$ 478
Delta
  • Delta
  • 4/12-5/12
  • 2 total stops
  • 13h 29m total
  • Montreal to Chicago
Search Deals
Delta
  • Delta
  • 14/12-31/12
  • 1 total stop
  • 10h 40m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 81 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 November 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

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$ 269

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 9/12

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$ 269

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 18/12

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$ 269

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 10/1

12:43 p.m.-10:17 p.m.

1 stop10h 34m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 269

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 5/12

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$ 270

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 11/1

6:00 a.m.-1:17 p.m.

1 stop8h 17m

Chicago Midway

Wed 31/12

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

Nonstop0h 00m

C$ 270
Quickest round-trip

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 1/12

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$ 270

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$ 270

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 8/12

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$ 284

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 30/11

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$ 284

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 21 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

Entertainment

6.9

Boarding

8.2

Comfort

8.0

Overall

8.0

Food

7.6

Crew

8.6

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

Entertainment

6.9

Boarding

8.2

Comfort

8.0

Overall

8.0

Food

7.6

Crew

8.6

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 fly from Montreal to Chicago Midway Airport in about 6h 25m. 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$ 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$ 465FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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