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YUL - MDW

C$ 199 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 Chicago departing on 4/12. 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, travellers 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 Chicago 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 Chicago

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

Recent one-way flight deals from Montreal to Chicago

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

Recent last-minute flight deals from Montreal to Chicago

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

Recent direct flight deals from Montreal to Chicago

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

Cheap bus & train deals from Montreal to Chicago

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

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
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10:45 a.m. - 4:40 p.m.YUL-MDW
6h 55m1 stop
12:05 p.m. - 6:00 p.m.MDW-YUL
4h 55m1 stop
C$ 346Porter Airlines
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Thu, 12 Dec - Mon, 16 Dec
6:50 a.m. - 11:10 a.m.YUL-MDW
5h 20m1 stop
12:05 p.m. - 7:20 p.m.MDW-YUL
6h 15m1 stop
C$ 350Porter Airlines
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Wed, 4 Dec - Fri, 6 Dec
11:50 a.m. - 4:40 p.m.YUL-MDW
5h 50m1 stop
11:15 a.m. - 6:00 p.m.MDW-YUL
5h 45m1 stop
C$ 352Porter Airlines
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Mon, 23 Dec - Wed, 1 Jan
6:50 a.m. - 10:20 a.m.YUL-MDW
4h 30m1 stop
11:25 a.m. - 6:00 p.m.MDW-YUL
5h 35m1 stop
C$ 353Porter Airlines
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Sun, 15 Dec - Thu, 19 Dec
6:00 a.m. - 1:35 p.m.YUL-MDW
8h 35m1 stop
12:44 p.m. - 11:55 p.m.MDW-YUL
10h 11m1 stop
C$ 381Delta
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Tue, 3 Dec - Thu, 12 Dec
7:00 a.m. - 11:58 a.m.YUL-MDW
5h 58m1 stop
1:30 p.m. - 11:11 p.m.MDW-YUL
8h 41m1 stop
C$ 384Delta
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Mon, 16 Dec - Wed, 18 Dec
6:00 a.m. - 6:11 p.m.YUL-MDW
13h 11m1 stop
9:20 a.m. - 11:37 p.m.MDW-YUL
13h 17m1 stop
C$ 435WestJet
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Tue, 18 Feb - Thu, 20 Feb
6:45 a.m. - 9:50 a.m.YUL-MDW
28h 05m2 stops
12:44 p.m. - 4:59 p.m.MDW-YUL
27h 15m1 stop
C$ 462WestJet
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Tue, 3 Dec - Sat, 7 Dec
6:55 a.m. - 10:20 a.m.YUL-MDW
4h 25m1 stop
9:20 a.m. - 11:24 p.m.MDW-YUL
13h 04m1 stop
C$ 480
Find Deal
Wed, 16 Apr - Sun, 20 Apr
6:30 p.m. - 9:50 a.m.YUL-MDW
16h 20m2 stops
12:05 p.m. - 6:00 p.m.MDW-YUL
4h 55m1 stop
C$ 496
Find Deal
Thu, 12 Dec - Mon, 16 Dec
6:50 a.m. - 11:10 a.m.YUL-MDW
5h 20m1 stop
C$ 199Porter Airlines
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Wed, 4 Dec
6:50 a.m. - 10:20 a.m.YUL-MDW
4h 30m1 stop
C$ 200Porter Airlines
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Fri, 29 Nov
6:50 a.m. - 12:00 p.m.YUL-MDW
6h 10m1 stop
C$ 207Porter Airlines
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Sat, 14 Dec
6:50 a.m. - 11:10 a.m.YUL-MDW
5h 20m1 stop
C$ 214Porter Airlines
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Wed, 4 Dec
6:00 a.m. - 1:35 p.m.YUL-MDW
8h 35m1 stop
C$ 231Delta
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Tue, 3 Dec
6:40 p.m. - 9:23 a.m.YUL-MDW
15h 43m1 stop
C$ 281WestJet
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Thu, 3 Apr
1:30 p.m. - 11:08 a.m.YUL-MDW
22h 38m2 stops
C$ 285WestJet
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Thu, 19 Dec
6:45 a.m. - 8:46 p.m.YUL-MDW
15h 01m2 stops
C$ 392
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Fri, 15 Nov
8:55 a.m. - 5:01 p.m.YUL-MDW
9h 06m2 stops
C$ 395
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Fri, 29 Nov
6:05 a.m. - 5:02 p.m.YUL-MDW
11h 57m2 stops
C$ 495Delta
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Mon, 25 Nov
11:50 a.m. - 4:40 p.m.YUL-MDW
5h 50m1 stop
11:15 a.m. - 6:00 p.m.MDW-YUL
5h 45m1 stop
C$ 506Porter Airlines
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Sun, 10 Nov - Sun, 17 Nov
6:50 a.m. - 12:00 p.m.YUL-MDW
6h 10m1 stop
11:15 a.m. - 6:00 p.m.MDW-YUL
5h 45m1 stop
C$ 623Porter Airlines
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Sat, 9 Nov - Tue, 12 Nov
10:45 a.m. - 4:40 p.m.YUL-MDW
6h 55m1 stop
11:15 a.m. - 4:45 p.m.MDW-YUL
4h 30m1 stop
C$ 627Porter Airlines
Find Deal
Thu, 7 Nov - Mon, 11 Nov
11:50 a.m. - 4:40 p.m.YUL-MDW
5h 50m1 stop
11:15 a.m. - 4:45 p.m.MDW-YUL
4h 30m1 stop
C$ 645Porter Airlines
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Thu, 7 Nov - Mon, 11 Nov
11:50 a.m. - 4:40 p.m.YUL-MDW
5h 50m1 stop
10:32 p.m. - 4:35 p.m.MDW-YUL
17h 03m1 stop
C$ 666
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Thu, 7 Nov - Mon, 11 Nov
6:45 a.m. - 9:38 p.m.YUL-MDW
15h 53m2 stops
12:43 p.m. - 11:45 a.m.MDW-YUL
22h 02m1 stop
C$ 724WestJet
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Sat, 9 Nov - Mon, 11 Nov
6:45 a.m. - 9:59 a.m.YUL-MDW
28h 14m2 stops
2:17 p.m. - 11:33 p.m.MDW-YUL
8h 16m1 stop
C$ 772WestJet
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Fri, 8 Nov - Mon, 11 Nov
6:00 a.m. - 12:32 p.m.YUL-MDW
7h 32m1 stop
12:43 p.m. - 11:59 p.m.MDW-YUL
10h 16m1 stop
C$ 972Delta
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Fri, 8 Nov - Mon, 11 Nov
6:50 a.m. - 10:20 a.m.YUL-MDW
4h 30m1 stop
7:55 p.m. - 11:15 p.m.MDW-YUL
26h 20m2 stops
C$ 1,100
Find Deal
Wed, 6 Nov - Wed, 6 Nov
7:05 a.m. - 5:03 p.m.YUL-MDW
10h 58m2 stops
2:17 p.m. - 11:33 p.m.MDW-YUL
8h 16m1 stop
C$ 1,404Delta
Find Deal
Sat, 9 Nov - Mon, 11 Nov

Flights from Montreal to Chicago - Travel Insights & Trends

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

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 C$ 349 on average. On the other hand, the most expensive months are October and August, where the average cost of tickets is C$ 642 and C$ 608 respectively.

Good to know

Low season

April

High season

June

Cheapest flight

C$ 199
Best time to beat the crowds (12% less expensive on average)
Most popular time to fly (5% more expensive on average)
Flight from Montreal to Chicago Midway Airport

When to book flights from Montreal to Chicago

Are your dates flexible? Find out the best times to travel from Montreal to Chicago 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 C$ 143 for a one-way ticket and C$ 249 for a round-trip.

  • 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 travellers 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.

  • 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 Chicago

 
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 Chicago? 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
8.5Crew
6.9Entertainment
7.9Comfort
7.6Food
8.0Boarding
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.
4/12Wed
1 stopPorter Airlines
5h 20mYUL-MDW
C$ 199
29/11Fri
1 stopPorter Airlines
4h 30mYUL-MDW
C$ 200
14/12Sat
1 stopPorter Airlines
6h 10mYUL-MDW
C$ 207
4/12Wed
1 stopPorter Airlines
5h 20mYUL-MDW
C$ 214
3/12Tue
1 stopDelta
8h 35mYUL-MDW
C$ 231
3/4Thu
1 stopWestJet
15h 43mYUL-MDW
C$ 281
19/12Thu
2 stopsWestJet
22h 38mYUL-MDW
C$ 285
15/11Fri
2 stops
15h 01mYUL-MDW
C$ 392
29/11Fri
2 stops
9h 06mYUL-MDW
C$ 395
25/11Mon
2 stopsDelta
11h 57mYUL-MDW
C$ 495

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Last minute flights from Montreal to Chicago

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.
10/11Sun
multi-stopPorter Airlines
5h 50mYUL-MDW
17/11Sun
multi-stopPorter Airlines
5h 45mMDW-YUL
C$ 506
9/11Sat
multi-stopPorter Airlines
6h 10mYUL-MDW
12/11Tue
multi-stopPorter Airlines
5h 45mMDW-YUL
C$ 623
7/11Thu
multi-stopPorter Airlines
6h 55mYUL-MDW
11/11Mon
multi-stopPorter Airlines
4h 30mMDW-YUL
C$ 627
7/11Thu
multi-stopPorter Airlines
5h 50mYUL-MDW
11/11Mon
multi-stopPorter Airlines
4h 30mMDW-YUL
C$ 645
7/11Thu
multi-stop
5h 50mYUL-MDW
11/11Mon
multi-stop
17h 03mMDW-YUL
C$ 666
9/11Sat
multi-stopWestJet
15h 53mYUL-MDW
11/11Mon
multi-stopWestJet
22h 02mMDW-YUL
C$ 724
8/11Fri
multi-stopWestJet
28h 14mYUL-MDW
11/11Mon
multi-stopWestJet
8h 16mMDW-YUL
C$ 772
8/11Fri
multi-stopDelta
7h 32mYUL-MDW
11/11Mon
multi-stopDelta
10h 16mMDW-YUL
C$ 972
6/11Wed
multi-stop
4h 30mYUL-MDW
6/11Wed
multi-stop
26h 20mMDW-YUL
C$ 1,100
9/11Sat
multi-stopDelta
10h 58mYUL-MDW
11/11Mon
multi-stopDelta
8h 16mMDW-YUL
C$ 1,404

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

Information on your arrival and departure airports

Midway (MDW)
Montreal (YUL)