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YUL - MDW

$143 Find Cheap Flights from Montreal to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Montreal to Midway departing on 12/4. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags

Search hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Montreal to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Montreal to Chicago, as well as popular online travel agencies
In the last 7 days travelers have searched 45,397,481 times on KAYAK, and here is why:

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Cheap Flight Deals from Montreal to Chicago Midway Airport (YUL-MDW)

 
These are the cheapest deals for flights from Montreal to Midway currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Montreal to Midway

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Montreal to Midway.

Recent one-way flight deals from Montreal to Midway

Only flying one-way? Below are some of the best one-way flight deals from Montreal to Midway found on KAYAK recently.

Recent last minute flight deals from Montreal to Midway

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from Montreal to Midway.

Recent direct flight deals from Montreal to Midway

The latest deals for direct flights from Montreal to Midway so you can sit back and relax without the need for a layover.

Cheap bus & train deals from Montreal to Midway

Find recent round-trip train or bus tickets from Montreal to Midway.

All round-trip flight deals to Midway

The cheapest plane tickets to Midway found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
11:50 am - 4:40 pmYUL-MDW
5h 50m1 stop
11:15 am - 4:45 pmMDW-YUL
4h 30m1 stop
$229Porter Airlines
Find Deal
Mon, Nov 25 - Wed, Nov 27
11:50 am - 4:40 pmYUL-MDW
5h 50m1 stop
12:05 pm - 7:20 pmMDW-YUL
6h 15m1 stop
$232Porter Airlines
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Thu, Nov 28 - Mon, Dec 2
6:50 am - 10:20 amYUL-MDW
4h 30m1 stop
12:55 pm - 6:15 pmMDW-YUL
4h 20m1 stop
$235Porter Airlines
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Thu, Nov 28 - Sat, Nov 30
6:50 am - 10:20 amYUL-MDW
4h 30m1 stop
12:55 pm - 6:15 pmMDW-YUL
4h 20m1 stop
$238Porter Airlines
Find Deal
Fri, Nov 29 - Sat, Dec 7
6:00 am - 1:35 pmYUL-MDW
8h 35m1 stop
12:44 pm - 11:55 pmMDW-YUL
10h 11m1 stop
$274Delta
Find Deal
Tue, Dec 3 - Thu, Dec 12
7:00 am - 11:58 amYUL-MDW
5h 58m1 stop
1:30 pm - 11:11 pmMDW-YUL
8h 41m1 stop
$276Delta
Find Deal
Mon, Dec 16 - Wed, Dec 18
6:00 am - 6:11 pmYUL-MDW
13h 11m1 stop
9:20 am - 11:37 pmMDW-YUL
13h 17m1 stop
$313WestJet
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Tue, Feb 18 - Thu, Feb 20
6:45 am - 9:50 amYUL-MDW
28h 05m2 stops
12:44 pm - 4:59 pmMDW-YUL
27h 15m1 stop
$332WestJet
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Tue, Dec 3 - Sat, Dec 7
6:55 am - 10:20 amYUL-MDW
4h 25m1 stop
9:20 am - 11:24 pmMDW-YUL
13h 04m1 stop
$345
Find Deal
Wed, Apr 16 - Sun, Apr 20
6:30 pm - 9:50 amYUL-MDW
16h 20m2 stops
12:05 pm - 6:00 pmMDW-YUL
4h 55m1 stop
$357
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Thu, Dec 12 - Mon, Dec 16
6:50 am - 11:10 amYUL-MDW
5h 20m1 stop
$143Porter Airlines
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Wed, Dec 4
6:50 am - 10:20 amYUL-MDW
4h 30m1 stop
$144Porter Airlines
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Fri, Nov 29
6:50 am - 11:10 amYUL-MDW
5h 20m1 stop
$154Porter Airlines
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Wed, Dec 4
6:50 am - 10:20 amYUL-MDW
4h 30m1 stop
$155Porter Airlines
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Sun, Nov 24
6:00 am - 1:35 pmYUL-MDW
8h 35m1 stop
$166Delta
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Tue, Dec 3
6:40 pm - 9:23 amYUL-MDW
15h 43m1 stop
$202WestJet
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Thu, Apr 3
1:30 pm - 11:08 amYUL-MDW
22h 38m2 stops
$205WestJet
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Thu, Dec 19
6:45 am - 8:46 pmYUL-MDW
15h 01m2 stops
$282
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Fri, Nov 15
8:55 am - 5:01 pmYUL-MDW
9h 06m2 stops
$284
Find Deal
Fri, Nov 29
6:05 am - 5:02 pmYUL-MDW
11h 57m2 stops
$356Delta
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Mon, Nov 25
11:50 am - 4:40 pmYUL-MDW
5h 50m1 stop
11:15 am - 6:00 pmMDW-YUL
5h 45m1 stop
$364Porter Airlines
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Sun, Nov 10 - Sun, Nov 17
6:50 am - 12:00 pmYUL-MDW
6h 10m1 stop
11:15 am - 6:00 pmMDW-YUL
5h 45m1 stop
$448Porter Airlines
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Sat, Nov 9 - Tue, Nov 12
10:45 am - 4:40 pmYUL-MDW
6h 55m1 stop
11:15 am - 4:45 pmMDW-YUL
4h 30m1 stop
$451Porter Airlines
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Thu, Nov 7 - Mon, Nov 11
11:50 am - 4:40 pmYUL-MDW
5h 50m1 stop
11:15 am - 4:45 pmMDW-YUL
4h 30m1 stop
$464Porter Airlines
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Thu, Nov 7 - Mon, Nov 11
11:50 am - 4:40 pmYUL-MDW
5h 50m1 stop
10:32 pm - 4:35 pmMDW-YUL
17h 03m1 stop
$479
Find Deal
Thu, Nov 7 - Mon, Nov 11
6:45 am - 9:38 pmYUL-MDW
15h 53m2 stops
7:17 pm - 11:33 pmMDW-YUL
27h 16m1 stop
$521WestJet
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Sat, Nov 9 - Tue, Nov 12
6:45 am - 9:59 amYUL-MDW
28h 14m2 stops
2:17 pm - 11:33 pmMDW-YUL
8h 16m1 stop
$555WestJet
Find Deal
Fri, Nov 8 - Mon, Nov 11
6:00 am - 12:32 pmYUL-MDW
7h 32m1 stop
12:43 pm - 11:59 pmMDW-YUL
10h 16m1 stop
$699Delta
Find Deal
Fri, Nov 8 - Mon, Nov 11
6:50 am - 10:20 amYUL-MDW
4h 30m1 stop
7:55 pm - 11:15 pmMDW-YUL
26h 20m2 stops
$791
Find Deal
Wed, Nov 6 - Wed, Nov 6
7:05 am - 5:03 pmYUL-MDW
10h 58m2 stops
2:17 pm - 11:33 pmMDW-YUL
8h 16m1 stop
$1,010Delta
Find Deal
Sat, Nov 9 - Mon, Nov 11

Flights from Montreal to Midway - Travel Insights & Trends

Get data-powered insights and trends into flights from Montreal to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Montreal to Chicago Midway Airport?

The average price of all flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
For Montreal to Chicago Midway Airport, Monday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago Midway Airport back to Montreal, the best deals are generally found on Sunday, with Monday being the most expensive.

What is the cheapest month to fly from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport is December, where tickets cost $251 on average. On the other hand, the most expensive months are October and August, where the average cost of tickets is $462 and $437 respectively.

Good to know

Low season

April

High season

June

Cheapest flight

$143
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Montreal to Chicago Midway Airport

When to book flights from Montreal to Midway

Are your dates flexible? Find out the best times to travel from Montreal to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Montreal to Chicago Midway Airport flights

  • What is the cheapest flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport was $143 for a one-way ticket and $229 for a round-trip.

  • Do I need a passport to fly between Montreal and Chicago Midway Airport?

    A passport is required to fly from Montreal to Chicago Midway Airport.

  • Which aircraft models fly most regularly from Montreal to Chicago Midway Airport?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Montreal to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between Montreal and Chicago Midway Airport.

  • How does KAYAK find such low prices on flights from Montreal to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Montreal to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Montreal to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Montreal is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Montreal to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Montreal with another airline. Booking your flights between Montreal and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Montreal to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Montreal up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top airline flying from Montreal to Midway

 
See real verified KAYAK customer reviews for airlines flying from Montreal to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Montreal to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.8
Porter AirlinesOverall score based on 293 reviews
7.6Food
8.5Crew
8.0Boarding
7.9Comfort
6.9Entertainment
Airline reviews

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

4.0 OkayAnonymous, Oct 2024YYZ - YOW
Read more Porter Airlines reviews

Thanks for giving a beer to everyone in the seat infront of me and then telling me that I can’t have one because they are going to land. I guess I need to pay for a seat and then pick one in the very front of the plane

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

Awesome, the whole way through. Thank you, this is the new Canadian Airline benchmark.

We were given a complimentary seat upgrade which was so unexpected but so lovely!

Porter was excellent. Boarding was a breeze. The seats were a little uncomfortably but the overall trip was excellent.

Only packaged snacks were served. It was a flight at lunchtime and a hot meal would have been a great.

Reserve check-in was very slow compared to regular check-in. Internet was slow

Lavatories broke with an hour to go. At least we were on time.

Chaotic boarding, but mostly my issues are with Toronto airport

Flight delayed by half hour, causing rush to get to connecting flight in Toronto Pearson which doesn’t have good flow for managing immigration check and connections.

Book cheap flights from Montreal to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Montreal to Chicago found on KAYAK in the last 72 hours.
12/4Wed
1 stopPorter Airlines
5h 20mYUL-MDW
$143
11/29Fri
1 stopPorter Airlines
4h 30mYUL-MDW
$144
12/4Wed
1 stopPorter Airlines
5h 20mYUL-MDW
$154
11/24Sun
1 stopPorter Airlines
4h 30mYUL-MDW
$155
12/3Tue
1 stopDelta
8h 35mYUL-MDW
$166
4/3Thu
1 stopWestJet
15h 43mYUL-MDW
$202
12/19Thu
2 stopsWestJet
22h 38mYUL-MDW
$205
11/15Fri
2 stops
15h 01mYUL-MDW
$282
11/29Fri
2 stops
9h 06mYUL-MDW
$284
11/25Mon
2 stopsDelta
11h 57mYUL-MDW
$356

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Last minute flights from Montreal to Midway

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Montreal to Chicago that are departing in the next 10 days.
11/10Sun
multi-stopPorter Airlines
5h 50mYUL-MDW
11/17Sun
multi-stopPorter Airlines
5h 45mMDW-YUL
$364
11/9Sat
multi-stopPorter Airlines
6h 10mYUL-MDW
11/12Tue
multi-stopPorter Airlines
5h 45mMDW-YUL
$448
11/7Thu
multi-stopPorter Airlines
6h 55mYUL-MDW
11/11Mon
multi-stopPorter Airlines
4h 30mMDW-YUL
$451
11/7Thu
multi-stopPorter Airlines
5h 50mYUL-MDW
11/11Mon
multi-stopPorter Airlines
4h 30mMDW-YUL
$464
11/7Thu
multi-stop
5h 50mYUL-MDW
11/11Mon
multi-stop
17h 03mMDW-YUL
$479
11/9Sat
multi-stopWestJet
15h 53mYUL-MDW
11/12Tue
multi-stopWestJet
27h 16mMDW-YUL
$521
11/8Fri
multi-stopWestJet
28h 14mYUL-MDW
11/11Mon
multi-stopWestJet
8h 16mMDW-YUL
$555
11/8Fri
multi-stopDelta
7h 32mYUL-MDW
11/11Mon
multi-stopDelta
10h 16mMDW-YUL
$699
11/6Wed
multi-stop
4h 30mYUL-MDW
11/6Wed
multi-stop
26h 20mMDW-YUL
$791
11/9Sat
multi-stopDelta
10h 58mYUL-MDW
11/11Mon
multi-stopDelta
8h 16mMDW-YUL
$1,010

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Everything you need to know for your flight from Montreal to Midway

Information on your arrival and departure airports

Midway (MDW)
Montreal (YUL)