Find flights
When to book
Airlines
FAQs

Cheap flights from Montreal to Chicago Midway Airport from C$ 233

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 14/12. Fares are subject to change and may not be available on all flights or dates of travel.
YMQ — MDW
3 Dec — 10 Dec1
1 adult
1 adult, Economy, 0 bags

Cheap 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 3 November 2025.

Round-trip from

C$ 326

One-way from

C$ 233

Popular in

December

Cheapest in

September

Average price

C$ 445
Porter Airlines
  • Porter Airlines
  • 2/4-7/4
  • 2 total stops
  • 12h 50m total
  • Montreal to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 14/12
  • 1 total stop
  • 4h 20m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 108 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Find 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 3 November 2025.

Tue 30/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Thu 1/14:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 2/11C$ 360
Fri 19/1211:25 a.m.YUL - MDW
1 stop4h 55mPorter Airlines
Sun 21/1211:00 a.m.MDW - YUL
1 stop5h 45mPorter Airlines
Deal found 2/11C$ 367
Thu 18/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Sat 3/14:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 1/11C$ 368
Fri 5/1211:25 a.m.YUL - MDW
1 stop4h 55mPorter Airlines
Mon 8/1211:00 a.m.MDW - YUL
1 stop6h 45mPorter Airlines
Deal found 2/11C$ 370
Sat 27/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Sat 3/14:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 1/11C$ 371
Fri 19/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Sat 3/111:00 a.m.MDW - YUL
1 stop5h 45mPorter Airlines
Deal found 2/11C$ 377
Fri 28/116:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Tue 2/1211:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 2/11C$ 378
Thu 4/126:45 a.m.YUL - MDW
1 stop4h 20mPorter Airlines
Sun 7/1211:00 a.m.MDW - YUL
1 stop5h 45mPorter Airlines
Deal found 2/11C$ 384
Tue 23/1211:25 a.m.YUL - MDW
1 stop4h 55mPorter Airlines
Sun 28/1211:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 2/11C$ 385
Fri 28/1111:25 a.m.YUL - MDW
1 stop4h 55mPorter Airlines
Mon 1/1211:00 a.m.MDW - YUL
1 stop6h 45mPorter Airlines
Deal found 1/11C$ 387
Mon 15/1211:25 a.m.YUL - MDW
1 stop4h 55mPorter Airlines
Sun 4/111:00 a.m.MDW - YUL
1 stop4h 30mPorter Airlines
Deal found 2/11C$ 394
Sat 22/118:55 a.m.YUL - MDW
1 stop3h 55mPorter Airlines
Mon 24/114:15 p.m.MDW - YUL
1 stop5h 30mPorter Airlines
Deal found 1/11C$ 402

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 3 November 2025.
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

Fri 5/12

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

1 stop4h 55m

Chicago Midway

Mon 8/12

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

1 stop6h 45m

C$ 370

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 16/12

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

1 stop4h 20m

Chicago Midway

Sun 4/1

11:00 a.m.-4:30 p.m.

1 stop4h 30m

C$ 377

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 15/12

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

1 stop4h 20m

Chicago Midway

Sat 3/1

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

1 stop5h 45m

C$ 394

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 2/12

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

1 stop4h 20m

Chicago Midway

Sun 7/12

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

1 stop6h 45m

C$ 405

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 19/12

10:15 a.m.-3:20 p.m.

1 stop6h 05m

Chicago Midway

Thu 1/1

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

1 stop5h 30m

C$ 415

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 2/4

10:15 a.m.-3:20 p.m.

1 stop6h 05m

Chicago Midway

Mon 6/4

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

1 stop5h 45m

C$ 416

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 25/11

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

1 stop4h 20m

Chicago Midway

Fri 28/11

11:00 a.m.-4:30 p.m.

1 stop4h 30m

C$ 420

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 23/11

6:26 p.m.-11:40 p.m.

1 stop6h 14m

Chicago Midway

Wed 26/11

5:34 p.m.-11:59 p.m.

1 stop5h 25m

C$ 423

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 23/11

6:26 p.m.-11:40 p.m.

1 stop6h 14m

Chicago Midway

Mon 1/12

5:34 p.m.-11:59 p.m.

1 stop5h 25m

C$ 423

MontrealChicago

YUL - MDW

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 7/12

6:00 a.m.-12:34 p.m.

1 stop7h 34m

Chicago Midway

Fri 12/12

5:13 p.m.-11:59 p.m.

1 stop5h 46m

C$ 423

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Showing 1-10 of 22 results
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

What is the cheapest month to book a flight from Montreal to Chicago Midway Airport?

Currently, September is the cheapest month in which you can book a flight from Montreal to Chicago Midway Airport (average of C$ 184). Flying from Montreal to Chicago Midway Airport in January is currently the most expensive (average of C$ 420). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Montreal to Chicago Midway Airport?

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 3 November 2025.
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
384 reviews
Check prices

Comfort

8.0

Food

7.6

Overall

8.0

Crew

8.6

Entertainment

7.0

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Porter Airlines
8.0
Very good
384 reviews
Porter Airlines
8.0
Very good
384 reviews
Check prices

Comfort

8.0

Food

7.6

Overall

8.0

Crew

8.6

Entertainment

7.0

Boarding

8.2

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

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 55m. 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$ 199, 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.

  • What is the cheapest month to book a flight from Montreal to Chicago Midway Airport?

    Currently, September is the cheapest month in which you can book a flight from Montreal to Chicago Midway Airport (average of C$ 184). Flying from Montreal to Chicago Midway Airport in January is currently the most expensive (average of C$ 420). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 3 November 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 199AverageC$ 449FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.