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YUL - MDW

C$ 239 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 19/4. 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, travellers have searched 46,646,933 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.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
6:00 a.m. - 5:47 p.m.YUL-MDW
12h 47m1 stop
10:19 a.m. - 11:36 p.m.MDW-YUL
12h 17m1 stop
C$ 429WestJet
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Fri, 24 Jan - Mon, 10 Feb
6:00 a.m. - 6:32 p.m.YUL-MDW
13h 32m1 stop
2:15 p.m. - 11:41 p.m.MDW-YUL
8h 26m1 stop
C$ 432WestJet
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Sun, 15 Dec - Tue, 17 Dec
11:50 a.m. - 4:40 p.m.YUL-MDW
5h 50m1 stop
5:35 p.m. - 10:30 p.m.MDW-YUL
3h 55m1 stop
C$ 435Porter Airlines
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Thu, 20 Mar - Sun, 23 Mar
10:45 a.m. - 4:40 p.m.YUL-MDW
6h 55m1 stop
11:25 a.m. - 7:20 p.m.MDW-YUL
6h 55m1 stop
C$ 437Porter Airlines
Find Deal
Mon, 23 Dec - Sat, 28 Dec
11:50 a.m. - 4:40 p.m.YUL-MDW
5h 50m1 stop
5:35 p.m. - 10:45 p.m.MDW-YUL
4h 10m1 stop
C$ 439Porter Airlines
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Thu, 27 Mar - Mon, 31 Mar
6:00 a.m. - 12:46 p.m.YUL-MDW
7h 46m1 stop
1:26 p.m. - 11:36 p.m.MDW-YUL
9h 10m1 stop
C$ 440WestJet
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Thu, 30 Jan - Wed, 5 Feb
5:35 p.m. - 11:48 a.m.YUL-MDW
19h 13m1 stop
5:35 p.m. - 10:45 p.m.MDW-YUL
4h 10m1 stop
C$ 538
Find Deal
Thu, 12 Dec - Mon, 16 Dec
5:35 p.m. - 11:48 a.m.YUL-MDW
19h 13m1 stop
12:05 p.m. - 6:00 p.m.MDW-YUL
4h 55m1 stop
C$ 544
Find Deal
Thu, 12 Dec - Mon, 16 Dec
12:50 p.m. - 5:01 p.m.YUL-MDW
5h 11m1 stop
5:50 p.m. - 11:11 p.m.MDW-YUL
4h 21m1 stop
C$ 551Delta
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Thu, 12 Dec - Mon, 16 Dec
7:10 a.m. - 12:49 p.m.YUL-MDW
6h 39m1 stop
5:50 p.m. - 11:11 p.m.MDW-YUL
4h 21m1 stop
C$ 572Delta
Find Deal
Tue, 3 Dec - Sat, 14 Dec

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 March, where tickets cost C$ 368 on average. On the other hand, the most expensive months are October and August, where the average cost of tickets is C$ 646 and C$ 611 respectively.

Good to know

Low season

April

High season

June

Cheapest flight

C$ 239
Best time to beat the crowds (12% less expensive on average)
Most popular time to fly (4% 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$ 171 for a one-way ticket and C$ 307 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 288 reviews
6.9Entertainment
8.6Crew
7.6Food
8.1Boarding
7.9Comfort
Airline reviews

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

10.0 ExcellentJoan, Nov 2024YOW - YYZ
Read more Porter Airlines reviews

The check-in staff, boarding staff, and flight crew were all very friendly. Really miss the Porter lounge in Ottawa.

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

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.
19/4Sat
1 stopWestJet
6h 15mYUL-MDW
C$ 239
4/12Wed
1 stopPorter Airlines
5h 20mYUL-MDW
C$ 243
24/4Thu
1 stopPorter Airlines
5h 50mYUL-MDW
C$ 250
17/12Tue
1 stopPorter Airlines
4h 30mYUL-MDW
C$ 263
25/12Wed
1 stopPorter Airlines
5h 50mYUL-MDW
C$ 264
17/12Tue
1 stopPorter Airlines
6h 55mYUL-MDW
C$ 266
11/12Wed
2 stops
22h 13mYUL-MDW
C$ 294
10/12Tue
2 stops
19h 07mYUL-MDW
C$ 348
29/3Sat
2 stopsDelta
11h 25mYUL-MDW
C$ 602
31/3Mon
2 stopsDelta
11h 25mYUL-MDW
C$ 650

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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.
24/11Sun
multi-stopWestJet
13h 32mYUL-MDW
27/11Wed
multi-stopWestJet
8h 16mMDW-YUL
C$ 567
26/11Tue
multi-stopPorter Airlines
4h 30mYUL-MDW
30/11Sat
multi-stopPorter Airlines
4h 20mMDW-YUL
C$ 591
25/11Mon
multi-stopPorter Airlines
5h 50mYUL-MDW
2/12Mon
multi-stopPorter Airlines
6h 15mMDW-YUL
C$ 601
25/11Mon
multi-stopPorter Airlines
5h 50mYUL-MDW
2/12Mon
multi-stopPorter Airlines
6h 15mMDW-YUL
C$ 630
22/11Fri
multi-stopPorter Airlines
4h 30mYUL-MDW
29/11Fri
multi-stopPorter Airlines
4h 30mMDW-YUL
C$ 632
25/11Mon
multi-stopPorter Airlines
4h 30mYUL-MDW
3/12Tue
multi-stopPorter Airlines
4h 30mMDW-YUL
C$ 637
23/11Sat
multi-stopDelta
6h 39mYUL-MDW
26/11Tue
multi-stopDelta
8h 41mMDW-YUL
C$ 728
22/11Fri
multi-stop
21h 46mYUL-MDW
29/11Fri
multi-stop
4h 30mMDW-YUL
C$ 797
22/11Fri
multi-stop
26h 11mYUL-MDW
24/11Sun
multi-stop
7h 10mMDW-YUL
C$ 1,138
25/11Mon
multi-stopDelta
5h 12mYUL-MDW
2/12Mon
multi-stopDelta
10h 37mMDW-YUL
C$ 1,785

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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)

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