Find flights
When to book
Airlines
FAQs

Cheap flights from Montreal to Chicago Midway Airport from C$ 274

YMQ — MDW
2 Dec — 9 Dec1
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

Thu 3/126:00 a.m. -
1 stop4h 37m
Sun 6/126:41 p.m. -
1 stop3h 52m
Deal found 28/10C$ 451
Fri 20/116:00 a.m. -
1 stop7h 51m
Mon 23/111:31 p.m. -
1 stop8h 56m
Deal found 1/11C$ 453
Tue 1/126:00 a.m. -
1 stop8h 01m
Tue 8/125:12 p.m. -
1 stop5h 36m
Deal found 1/11C$ 468
Thu 3/126:00 a.m. -
1 stop4h 37m
Sun 6/126:41 p.m. -
1 stop3h 52m
Deal found 28/10C$ 469
Fri 20/116:00 a.m. -
1 stop7h 51m
Mon 23/116:00 a.m. -
1 stop10h 27m
Deal found 31/10C$ 471
Thu 19/117:00 a.m. -
1 stop5h 59m
Mon 23/111:31 p.m. -
1 stop8h 56m
Deal found 30/10C$ 472
Thu 26/116:00 a.m. -
1 stop6h 25m
Mon 30/1112:30 p.m. -
1 stop10h 00m
Deal found 2/11C$ 482
Wed 18/116:00 a.m. -
1 stop4h 46m
Mon 23/116:44 p.m. -
1 stop3h 43m
Deal found 29/10C$ 490
Wed 25/117:00 a.m. -
1 stop10h 18m
Sun 29/116:00 a.m. -
1 stop10h 27m
Deal found 30/10C$ 492

Find flight deals from Montreal to Midway

Round-trip from

C$ 451

One-way from

C$ 274

Popular in

July

Cheapest in

April

Average price

C$ 483
KLM
  • KLM
  • 3/12-6/12
  • 2 total stops
  • 8h 29m total
  • Montreal to Chicago
Search Deals
Delta
  • Delta
  • 27/11-31/12
  • 1 total stop
  • 6h 25m total
  • Montreal to Chicago
Search Deals
Highest demand for flights based on searches. 10% potential increase in price (C$ 77 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (C$ 16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2026
Search Deals

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

Thu 10/12

6:00 a.m.-1:01 p.m.

1 stop8h 01m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 277
Quickest round-trip

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Wed 16/12

6:00 a.m.-9:37 a.m.

1 stop4h 37m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 277

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Tue 15/12

6:00 a.m.-1:01 p.m.

1 stop8h 01m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 277

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 15/11

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

1 stop7h 51m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 277

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 30/11

7:00 a.m.-4:18 p.m.

1 stop10h 18m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 278

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Thu 17/12

6:00 a.m.-1:01 p.m.

1 stop8h 01m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 282

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 14/12

7:00 a.m.-4:16 p.m.

1 stop10h 16m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 286

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Mon 16/11

7:00 a.m.-4:18 p.m.

1 stop10h 18m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 286

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Fri 27/11

6:00 a.m.-11:25 a.m.

1 stop6h 25m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 288

MontrealChicago

YUL Montreal Pierre Elliott Trudeau Intl - MDW Chicago Midway

YULMDW

Montreal Pierre Elliott Trudeau Intl

Sun 22/11

7:00 a.m.-4:18 p.m.

1 stop10h 18m

Chicago Midway

Wed 31/12

12:00 a.m.-1:00 a.m.

Nonstop0h 00m

C$ 314

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/10

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

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
467 reviews
Check prices

Overall

8.0

Crew

8.6

Food

7.6

Comfort

8.0

Boarding

8.2

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Porter Airlines
8.0
Very good
467 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Overall

8.0

Crew

8.6

Food

7.6

Comfort

8.0

Boarding

8.2

Entertainment

6.9

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Related info for your journey

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

    Airlines like Delta fly from Montreal to Chicago Midway Airport in about 6h 25m. 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$ 244, 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$ 244AverageC$ 457FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

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.