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Cheap flights from Montreal to Chicago Midway Airport from C$ 224

YMQ — MDW
20 Sep — 27 Sep1
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

Sun 27/910:35 a.m. -
1 stop5h 00m
Wed 30/911:45 a.m. -
1 stop5h 27m
Deal found 20/8C$ 374
Fri 16/106:30 a.m. -
1 stop5h 30m
Fri 16/103:20 p.m. -
1 stop4h 52m
Deal found 16/8C$ 377
Sat 5/910:20 a.m. -
1 stop5h 15m
Tue 8/911:45 a.m. -
1 stop5h 27m
Deal found 17/8C$ 378
Sat 5/910:20 a.m. -
1 stop5h 15m
Sat 12/911:45 a.m. -
1 stop5h 27m
Deal found 20/8C$ 383
Fri 18/96:30 a.m. -
1 stop5h 30m
Wed 23/93:20 p.m. -
1 stop4h 52m
Deal found 17/8C$ 384
Wed 2/910:35 a.m. -
1 stop5h 00m
Wed 9/911:45 a.m. -
1 stop5h 27m
Deal found 17/8C$ 385
Fri 25/99:00 a.m. -
1 stop6h 35m
Mon 28/911:45 a.m. -
1 stop5h 27m
Deal found 17/8C$ 388
Thu 17/99:00 a.m. -
1 stop6h 35m
Sun 20/93:20 p.m. -
1 stop4h 52m
Deal found 19/8C$ 391

Find flight deals from Montreal to Midway

Round-trip from

C$ 374

One-way from

C$ 224

Popular in

July

Cheapest in

April

Average price

C$ 497
Porter Airlines
  • Porter Airlines
  • 27/9-30/9
  • 2 total stops
  • 10h 27m total
  • Montreal to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 28/9
  • 1 total stop
  • 5h 30m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 85 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 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

Fri 11/9

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

1 stop6h 35m

Chicago Midway

Sun 13/9

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

1 stop5h 27m

C$ 394

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 2/9

6:00 a.m.-9:17 a.m.

1 stop4h 17m

Chicago Midway

Sun 6/9

5:45 p.m.-11:30 p.m.

1 stop4h 45m

C$ 433

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 28/10

6:00 a.m.-9:17 a.m.

1 stop4h 17m

Chicago Midway

Sat 31/10

5:31 p.m.-11:22 p.m.

1 stop4h 51m

C$ 449

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 10/9

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

1 stop5h 30m

Chicago Midway

Sun 13/9

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

1 stop5h 27m

C$ 449

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$ 449

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

Thu 29/10

6:44 p.m.-11:25 p.m.

1 stop3h 41m

C$ 451

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 5/9

6:00 a.m.-9:17 a.m.

1 stop4h 17m

Chicago Midway

Sun 6/9

5:45 p.m.-11:30 p.m.

1 stop4h 45m

C$ 454
Quickest round-trip

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 22/10

6:00 a.m.-9:17 a.m.

1 stop4h 17m

Chicago Midway

Sun 25/10

6:44 p.m.-11:25 p.m.

1 stop3h 41m

C$ 455

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 14/11

6:00 a.m.-12:35 p.m.

1 stop7h 35m

Chicago Midway

Sat 28/11

6:44 p.m.-11:26 p.m.

1 stop3h 42m

C$ 472
Cheapest one-way

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 28/9

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

1 stop5h 30m

C$ 224

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/8

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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
457 reviews
Check prices

Food

7.6

Overall

8.0

Entertainment

6.9

Crew

8.6

Comfort

8.0

Boarding

8.2

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
457 reviews
Porter Airlines
8.0
Very good
457 reviews
Check prices

Food

7.6

Overall

8.0

Entertainment

6.9

Crew

8.6

Comfort

8.0

Boarding

8.2

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 17m. The time it takes to get you to your destination can typically vary by up to 2h 18m. 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$ 241, 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$ 241AverageC$ 405FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

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Can Cheapflights find flights from Montreal to Midway with no change fees?

Need flexible booking options for your flight to Midway from Montreal? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Montreal to Midway become cheaper?

Yes, Cheapflights offers price alerts on Montreal to Midway flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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