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Cheap flights from Montreal to Chicago Midway Airport from C$ 158

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 29/3. Fares are subject to change and may not be available on all flights or dates of travel.
YMQ — MDW
18 Mar — 25 Mar1
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 16 February 2026.

Thu 16/46:45 a.m.
YUL
-
MDW
1 stop4h 20m
Porter Airlines
Sun 19/411:00 a.m.
MDW
-
YUL
1 stop5h 45m
Porter Airlines
Deal found 14/2C$ 227
Sat 18/48:55 a.m.
YUL
-
MDW
1 stop3h 55m
Porter Airlines
Mon 20/44:15 p.m.
MDW
-
YUL
1 stop5h 30m
Porter Airlines
Deal found 14/2C$ 230
Fri 8/56:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Mon 11/510:25 a.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 13/2C$ 236
Fri 10/411:25 a.m.
YUL
-
MDW
1 stop4h 55m
Porter Airlines
Fri 17/411:00 a.m.
MDW
-
YUL
1 stop6h 45m
Porter Airlines
Deal found 14/2C$ 241
Thu 26/36:50 a.m.
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Sun 29/34:15 p.m.
MDW
-
YUL
1 stop5h 30m
Porter Airlines
Deal found 12/2C$ 242
Mon 23/36:50 a.m.
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Wed 25/311:00 a.m.
MDW
-
YUL
1 stop4h 30m
Porter Airlines
Deal found 13/2C$ 244
Mon 30/36:50 a.m.
YUL
-
MDW
1 stop4h 15m
Porter Airlines
Mon 6/44:15 p.m.
MDW
-
YUL
1 stop5h 30m
Porter Airlines
Deal found 13/2C$ 246
Mon 27/46:45 a.m.
YUL
-
MDW
1 stop4h 20m
Porter Airlines
Fri 1/510:25 a.m.
MDW
-
YUL
1 stop6h 50m
Porter Airlines
Deal found 12/2C$ 263
Fri 3/48:55 a.m.
YUL
-
MDW
1 stop7h 25m
Porter Airlines
Sun 5/411:00 a.m.
MDW
-
YUL
1 stop4h 30m
Porter Airlines
Deal found 13/2C$ 267
Sun 26/48:55 a.m.
YUL
-
MDW
1 stop7h 25m
Porter Airlines
Mon 4/510:25 a.m.
MDW
-
YUL
1 stop5h 50m
Porter Airlines
Deal found 14/2C$ 271
Fri 8/56:30 a.m.
YUL
-
MDW
1 stop4h 10m
Porter Airlines
Sun 10/510:25 a.m.
MDW
-
YUL
1 stop8h 45m
Porter Airlines
Deal found 14/2C$ 272

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 16 February 2026.

Round-trip from

C$ 227

One-way from

C$ 158

Popular in

November

Cheapest in

September

Average price

C$ 249
Porter Airlines
  • Porter Airlines
  • 16/4-19/4
  • 2 total stops
  • 10h 05m total
  • Montreal to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 29/3
  • 1 total stop
  • 6h 30m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 19% potential increase in price (C$ 123 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 30 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 16 February 2026.
Use the filters below to find and compare flights from Montreal to Chicago Midway Airport that are best for you.

Fly from

Montreal

Fly to

Midway

Route

Depart

Return

Price

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 16/4

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

Sun 19/4

11:00 a.m.-5:45 p.m.

1 stop5h 45m

C$ 227

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sat 18/4

8:55 a.m.-11:50 a.m.

1 stop3h 55m

Chicago Midway

Mon 20/4

4:15 p.m.-10:45 p.m.

1 stop5h 30m

C$ 230

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 25/3

6:50 a.m.-10:05 a.m.

1 stop4h 15m

Chicago Midway

Sun 29/3

4:15 p.m.-10:45 p.m.

1 stop5h 30m

C$ 241

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 10/4

11:25 a.m.-3:20 p.m.

1 stop4h 55m

Chicago Midway

Fri 17/4

11:00 a.m.-6:45 p.m.

1 stop6h 45m

C$ 241

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 26/3

6:50 a.m.-10:05 a.m.

1 stop4h 15m

Chicago Midway

Sun 29/3

4:15 p.m.-10:45 p.m.

1 stop5h 30m

C$ 242

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 11/5

6:30 a.m.-9:40 a.m.

1 stop4h 10m

Chicago Midway

Fri 15/5

10:25 a.m.-8:10 p.m.

1 stop8h 45m

C$ 263

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 27/4

6:45 a.m.-10:05 a.m.

1 stop4h 20m

Chicago Midway

Fri 1/5

10:25 a.m.-6:15 p.m.

1 stop6h 50m

C$ 263

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 20/5

6:30 a.m.-9:40 a.m.

1 stop4h 10m

Chicago Midway

Sun 24/5

10:25 a.m.-5:15 p.m.

1 stop5h 50m

C$ 291

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 4/5

6:30 a.m.-9:40 a.m.

1 stop4h 10m

Chicago Midway

Wed 6/5

10:25 a.m.-5:15 p.m.

1 stop5h 50m

C$ 291

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 3/5

10:35 a.m.-4:50 p.m.

1 stop7h 15m

Chicago Midway

Mon 4/5

10:25 a.m.-5:15 p.m.

1 stop5h 50m

C$ 291

Flights are sorted by cheapest round-trip flights first.

Deals found on 15/2

Showing 1-10 of 21 results
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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
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 16 February 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
7.9
Good
416 reviews
Check prices

Comfort

7.9

Crew

8.6

Entertainment

6.9

Boarding

8.2

Food

7.5

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Jason,Feb 2026

PHX - YVR

This was my first flight with Porter Airlines. My only complaint was that I got an unpleasant surprise when I checked in at the counter at the airport. When I purchased my ticket online at the airline website, I had used a virtual credit card and my reservation was accepted. But the agent at the counter informed me that there was an issue with my payment method and that I would need to pay with a physical debit or credit card. The airline would reimburse me within 5 to 7 business days. I’m curious why my original payment was accepted if Porter doesn’t honor virtual payment cards.
Porter Airlines
7.9
Good
416 reviews
Porter Airlines
7.9
Good
416 reviews
Check prices

Comfort

7.9

Crew

8.6

Entertainment

6.9

Boarding

8.2

Food

7.5

Overall

7.9

Reviews

1 / 20
10.0
Excellent

Jason,Feb 2026

PHX - YVR

This was my first flight with Porter Airlines. My only complaint was that I got an unpleasant surprise when I checked in at the counter at the airport. When I purchased my ticket online at the airline website, I had used a virtual credit card and my reservation was accepted. But the agent at the counter informed me that there was an issue with my payment method and that I would need to pay with a physical debit or credit card. The airline would reimburse me within 5 to 7 business days. I’m curious why my original payment was accepted if Porter doesn’t honor virtual payment cards.

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 Porter Airlines fly from Montreal to Chicago Midway Airport in about 4h 20m. 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$ 186, was found to be the cheapest airline from Montreal to Chicago Midway Airport.. You may be able to fly from Montreal to Chicago Midway Airport for 50% less than the average price by searching for this airline.

  • 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 16 February 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 186AverageC$ 375FlexibilityNo 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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