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Cheap flights from Montreal to Chicago Midway Airport from C$ 232

YMQ — MDW
26 Sep — 3 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

Thu 17/99:00 a.m. -
1 stop6h 35m
Sun 20/93:20 p.m. -
1 stop4h 52m
Deal found 25/8C$ 384
Mon 14/96:30 a.m. -
1 stop5h 30m
Sat 10/1011:45 a.m. -
1 stop5h 27m
Deal found 22/8C$ 387
Fri 2/106:30 a.m. -
1 stop5h 30m
Mon 5/1011:45 a.m. -
1 stop5h 27m
Deal found 23/8C$ 390
Fri 25/99:00 a.m. -
1 stop6h 35m
Mon 28/911:45 a.m. -
1 stop5h 27m
Deal found 25/8C$ 391
Fri 25/99:00 a.m. -
1 stop6h 35m
Sun 27/93:20 p.m. -
1 stop4h 52m
Deal found 25/8C$ 392
Wed 23/99:00 a.m. -
1 stop6h 35m
Wed 30/911:45 a.m. -
1 stop5h 27m
Deal found 26/8C$ 395
Sat 26/96:30 a.m. -
1 stop5h 30m
Sat 3/1011:45 a.m. -
1 stop5h 27m
Deal found 26/8C$ 397
Sat 12/96:30 a.m. -
1 stop5h 30m
Tue 15/911:45 a.m. -
1 stop5h 27m
Deal found 22/8C$ 398
Wed 7/109:00 a.m. -
1 stop6h 35m
Thu 8/103:20 p.m. -
1 stop4h 52m
Deal found 25/8C$ 399
Sat 12/96:30 a.m. -
1 stop5h 30m
Wed 16/911:45 a.m. -
1 stop5h 27m
Deal found 23/8C$ 401
Mon 14/96:30 a.m. -
1 stop5h 30m
Wed 16/911:45 a.m. -
1 stop5h 27m
Deal found 24/8C$ 402

Find flight deals from Montreal to Midway

Round-trip from

C$ 384

One-way from

C$ 232

Popular in

July

Cheapest in

April

Average price

C$ 501
Porter Airlines
  • Porter Airlines
  • 17/9-20/9
  • 2 total stops
  • 11h 27m total
  • Montreal to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 23/9
  • 1 total stop
  • 6h 35m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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

Sat 12/9

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

1 stop5h 30m

Chicago Midway

Sun 13/9

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

1 stop4h 52m

C$ 399

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 8/12

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

1 stop4h 37m

Chicago Midway

Thu 10/12

1:41 p.m.-11:33 p.m.

1 stop8h 52m

C$ 438

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 17/11

6:00 a.m.-12:51 p.m.

1 stop7h 51m

Chicago Midway

Sun 22/11

1:31 p.m.-11:27 p.m.

1 stop8h 56m

C$ 440

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 25/9

9:00 a.m.-2:35 p.m.

1 stop6h 35m

Chicago Midway

Sun 27/9

11:45 a.m.-6:12 p.m.

1 stop5h 27m

C$ 452

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 17/10

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

1 stop5h 30m

Chicago Midway

Tue 20/10

11:45 a.m.-6:12 p.m.

1 stop5h 27m

C$ 452

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 16/11

6:00 a.m.-12:51 p.m.

1 stop7h 51m

Chicago Midway

Sun 22/11

6:44 p.m.-11:27 p.m.

1 stop3h 43m

C$ 459
Quickest round-trip

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 18/11

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

1 stop4h 42m

Chicago Midway

Mon 23/11

6:44 p.m.-11:27 p.m.

1 stop3h 43m

C$ 462

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 28/10

7:00 a.m.-11:47 a.m.

1 stop5h 47m

Chicago Midway

Tue 3/11

6:04 a.m.-1:39 p.m.

1 stop6h 35m

C$ 462

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 22/10

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

1 stop7h 47m

Chicago Midway

Sun 25/10

1:27 p.m.-11:25 p.m.

1 stop8h 58m

C$ 462

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 20/11

7:10 a.m.-4:39 p.m.

1 stop10h 29m

Chicago Midway

Mon 23/11

6:44 p.m.-11:27 p.m.

1 stop3h 43m

C$ 494

Flights are sorted by cheapest round-trip flights first.

Deals found on 24/8

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
458 reviews
Check prices

Entertainment

6.9

Boarding

8.2

Comfort

8.0

Food

7.6

Overall

8.0

Crew

8.6

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

Entertainment

6.9

Boarding

8.2

Comfort

8.0

Food

7.6

Overall

8.0

Crew

8.6

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 4h 37m. The time it takes to get you to your destination can typically vary by up to 53m. 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$ 243, 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$ 243AverageC$ 408FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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