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Cheap flights from Montreal to Chicago Midway Airport from C$ 228

YMQ — MDW
2 Oct — 9 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

Mon 21/99:00 a.m. -
1 stop6h 35m
Sat 26/911:45 a.m. -
1 stop5h 27m
Deal found 30/8C$ 389
Sat 19/96:30 a.m. -
1 stop5h 30m
Sun 20/911:45 a.m. -
1 stop5h 27m
Deal found 29/8C$ 390
Fri 25/99:00 a.m. -
1 stop6h 35m
Mon 28/911:45 a.m. -
1 stop5h 27m
Deal found 28/8C$ 391
Tue 22/99:00 a.m. -
1 stop6h 35m
Sat 26/911:45 a.m. -
1 stop5h 27m
Deal found 28/8C$ 393
Wed 14/106:30 a.m. -
1 stop5h 30m
Thu 15/103:20 p.m. -
1 stop4h 52m
Deal found 27/8C$ 396
Mon 21/99:00 a.m. -
1 stop6h 35m
Thu 24/93:20 p.m. -
1 stop4h 52m
Deal found 29/8C$ 398
Fri 2/109:00 a.m. -
1 stop6h 35m
Sun 4/103:20 p.m. -
1 stop4h 52m
Deal found 30/8C$ 400
Sat 26/96:30 a.m. -
1 stop5h 30m
Tue 29/93:20 p.m. -
1 stop4h 52m
Deal found 1/9C$ 401
Fri 18/99:00 a.m. -
1 stop6h 35m
Sun 20/911:45 a.m. -
1 stop5h 27m
Deal found 28/8C$ 404
Tue 15/99:00 a.m. -
1 stop6h 35m
Tue 22/911:45 a.m. -
1 stop5h 27m
Deal found 30/8C$ 405

Find flight deals from Montreal to Midway

Round-trip from

C$ 389

One-way from

C$ 228

Popular in

July

Cheapest in

April

Average price

C$ 407
Porter Airlines
  • Porter Airlines
  • 21/9-26/9
  • 2 total stops
  • 12h 02m total
  • Montreal to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 26/9
  • 1 total stop
  • 5h 30m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 11% potential increase in price (C$ 86 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 September 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

Sun 11/10

10:35 a.m.-2:35 p.m.

1 stop5h 00m

Chicago Midway

Sat 17/10

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

1 stop5h 27m

C$ 408

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$ 439
Quickest round-trip

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 25/9

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

1 stop5h 30m

Chicago Midway

Tue 29/9

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

1 stop4h 52m

C$ 451

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 24/9

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

1 stop6h 35m

Chicago Midway

Tue 29/9

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

1 stop5h 27m

C$ 451

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 7/10

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

1 stop5h 30m

Chicago Midway

Wed 14/10

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

1 stop4h 52m

C$ 451

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 26/9

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

1 stop5h 30m

Chicago Midway

Mon 28/9

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

1 stop5h 27m

C$ 451

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$ 453

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 21/11

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

1 stop7h 51m

Chicago Midway

Mon 30/11

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

1 stop8h 56m

C$ 458

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 7/10

6:00 a.m.-9:32 a.m.

1 stop4h 32m

Chicago Midway

Tue 13/10

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

1 stop8h 58m

C$ 458

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 23/10

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

1 stop7h 47m

Chicago Midway

Mon 26/10

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

1 stop8h 58m

C$ 458

Flights are sorted by cheapest round-trip flights first.

Deals found on 29/8

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

Food

7.6

Comfort

8.0

Crew

8.6

Overall

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
458 reviews
Porter Airlines
8.0
Very good
458 reviews
Check prices

Entertainment

6.9

Food

7.6

Comfort

8.0

Crew

8.6

Overall

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 37m. The time it takes to get you to your destination can typically vary by up to 23m. 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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