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Cheap flights from Montreal to Chicago Midway Airport from C$ 226

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
YMQ — MDW
16 Sep — 23 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
Explore the most affordable flight options available from Montreal to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 17 August 2026.

Fri 18/99:00 a.m. -
1 stop6h 35m
Mon 21/93:20 p.m. -
1 stop4h 52m
Deal found 12/8C$ 380
Sat 5/910:20 a.m. -
1 stop5h 15m
Tue 8/911:45 a.m. -
1 stop5h 27m
Deal found 15/8C$ 381
Wed 30/96:30 a.m. -
1 stop5h 30m
Wed 7/103:20 p.m. -
1 stop4h 52m
Deal found 16/8C$ 383
Sat 5/910:20 a.m. -
1 stop5h 15m
Sat 12/911:45 a.m. -
1 stop5h 27m
Deal found 16/8C$ 384
Sat 19/96:30 a.m. -
1 stop5h 30m
Sun 20/93:20 p.m. -
1 stop4h 52m
Deal found 14/8C$ 386
Fri 4/96:30 a.m. -
1 stop5h 30m
Tue 8/93:20 p.m. -
1 stop4h 52m
Deal found 13/8C$ 387
Fri 25/99:00 a.m. -
1 stop6h 35m
Mon 28/911:45 a.m. -
1 stop5h 27m
Deal found 14/8C$ 390
Wed 9/99:00 a.m. -
1 stop6h 35m
Mon 14/911:45 a.m. -
1 stop5h 27m
Deal found 15/8C$ 393
Thu 22/106:30 a.m. -
1 stop5h 30m
Sat 24/1011:45 a.m. -
1 stop5h 27m
Deal found 17/8C$ 394
Fri 25/99:00 a.m. -
1 stop6h 35m
Sun 27/93:20 p.m. -
1 stop4h 52m
Deal found 13/8C$ 395
Fri 11/99:00 a.m. -
1 stop6h 35m
Sun 13/911:45 a.m. -
1 stop5h 27m
Deal found 16/8C$ 397

Find flight deals from Montreal to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Montreal (YMQ) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 17 August 2026.

Round-trip from

C$ 380

One-way from

C$ 226

Popular in

July

Cheapest in

April

Average price

C$ 501
Porter Airlines
  • Porter Airlines
  • 18/9-21/9
  • 2 total stops
  • 11h 27m total
  • Montreal to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 3/9
  • 1 total stop
  • 5h 30m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (C$ 86 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
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Montreal to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 17 August 2026.
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 29/8

12:47 p.m.-6:33 p.m.

1 stop6h 46m

Chicago Midway

Wed 2/9

4:39 p.m.-11:52 p.m.

1 stop6h 13m

C$ 405

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 23/10

7:00 a.m.-11:50 a.m.

1 stop5h 50m

Chicago Midway

Sat 24/10

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

1 stop3h 41m

C$ 430

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 27/10

7:00 a.m.-11:50 a.m.

1 stop5h 50m

Chicago Midway

Sun 1/11

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

1 stop8h 58m

C$ 430

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 4/9

6:00 a.m.-12:39 p.m.

1 stop7h 39m

Chicago Midway

Sat 5/9

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

1 stop4h 45m

C$ 430

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$ 452

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 10/10

7:00 a.m.-3:17 p.m.

1 stop9h 17m

Chicago Midway

Sat 17/10

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

1 stop3h 41m

C$ 452

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 23/10

7:00 a.m.-4:19 p.m.

1 stop10h 19m

Chicago Midway

Tue 27/10

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

1 stop4h 51m

C$ 454

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 22/10

12:50 p.m.-6:00 p.m.

1 stop6h 10m

Chicago Midway

Mon 26/10

5:15 p.m.-11:59 p.m.

1 stop5h 44m

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$ 459

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 3/9

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

1 stop5h 30m

Chicago Midway

Fri 11/9

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

1 stop4h 52m

C$ 476

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/8

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

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

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated 17 August 2026.
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

Comfort

8.0

Crew

8.6

Entertainment

6.9

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

Comfort

8.0

Crew

8.6

Entertainment

6.9

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

Find useful and relevant information for your journey from Montreal to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Montreal to Chicago Midway Airport?

    Airlines like Delta fly from Montreal to Chicago Midway Airport in about 6h 46m. 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$ 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

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Top airline flying from Montreal to Midway

Discover the top airline that operate flights from Montreal to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 17 August 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 243AverageC$ 408FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Montreal to Midway?

Cheapflights makes it easy to find Montreal to Midway flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Montreal to Midway?

Cheapflights helps you find that perfect flight to Midway from Montreal by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

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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