YUL - MDW

C$ 178 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 10/9. 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
1 adult, Economy

KAYAK searches 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
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Flights Deals

Cheap Flights from Montreal to Midway (YUL-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Montreal to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Montreal to Chicago

Fri, 3 Oct - Sun, 5 Oct
Porter Airlines Logo
10:45 a.m. - 4:24 p.m.YUL-MDW
6h 39m1 stop
Porter Airlines Logo
5:20 p.m. - 10:15 p.m.MDW-YUL
3h 55m1 stop
C$ 273Porter Airlines
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Thu, 2 Oct - Fri, 10 Oct
Porter Airlines Logo
1:10 p.m. - 4:24 p.m.YUL-MDW
4h 14m1 stop
Porter Airlines Logo
5:20 p.m. - 10:15 p.m.MDW-YUL
3h 55m1 stop
C$ 276Porter Airlines
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Thu, 18 Sep - Sat, 27 Sep
Porter Airlines Logo
1:10 p.m. - 4:24 p.m.YUL-MDW
4h 14m1 stop
Porter Airlines Logo
9:35 a.m. - 5:55 p.m.MDW-YUL
7h 20m1 stop
C$ 283Porter Airlines
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Wed, 8 Oct - Wed, 15 Oct
Porter Airlines Logo
1:10 p.m. - 4:24 p.m.YUL-MDW
4h 14m1 stop
Porter Airlines Logo
9:35 a.m. - 4:00 p.m.MDW-YUL
5h 25m1 stop
C$ 287Porter Airlines
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Thu, 18 Sep - Sun, 21 Sep
Porter Airlines Logo
10:45 a.m. - 4:24 p.m.YUL-MDW
6h 39m1 stop
Porter Airlines Logo
5:20 p.m. - 10:15 p.m.MDW-YUL
3h 55m1 stop
C$ 290Porter Airlines
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Wed, 3 Sep - Sat, 6 Sep
Delta Logo
6:00 a.m. - 8:35 a.m.YUL-MDW
3h 35m1 stop
Delta Logo
6:00 a.m. - 1:38 p.m.MDW-YUL
6h 38m1 stop
C$ 297Delta
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Sat, 13 Sep - Sat, 20 Sep
Delta Logo
7:00 a.m. - 3:26 p.m.YUL-MDW
9h 26m1 stop
Delta Logo
4:25 p.m. - 11:56 p.m.MDW-YUL
6h 31m1 stop
C$ 298Delta
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Fri, 17 Oct - Tue, 21 Oct
Porter Airlines Logo
1:10 p.m. - 4:24 p.m.YUL-MDW
4h 14m1 stop
Porter Airlines Logo
9:35 a.m. - 4:00 p.m.MDW-YUL
5h 25m1 stop
C$ 313Porter Airlines
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Thu, 28 Aug - Tue, 2 Sep
Porter Airlines Logo
10:45 a.m. - 4:24 p.m.YUL-MDW
6h 39m1 stop
Porter Airlines Logo
5:20 p.m. - 10:15 p.m.MDW-YUL
3h 55m1 stop
C$ 315Porter Airlines
Find Deal
Thu, 21 Aug - Tue, 26 Aug
Porter Airlines Logo
10:45 a.m. - 4:24 p.m.YUL-MDW
6h 39m1 stop
Porter Airlines Logo
5:20 p.m. - 10:15 p.m.MDW-YUL
3h 55m1 stop
C$ 316Porter Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Montreal to Chicago flights

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 round-trip 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 September, where tickets cost C$ 255 (return) on average. On the other hand, the most expensive months are October and July, where the average cost of round-trip tickets is C$ 595 and C$ 528 respectively.

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Good to know

Low seasonMarch
Cheapest flightC$ 178
Best time to beat the crowds but there is an average 3% increase in price.
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$ 129 for a one-way ticket and C$ 198 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.

Reviews of the 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.
8.0
Porter AirlinesOverall score based on 318 reviews
7.0Entertainment
8.0Comfort
8.2Boarding
7.6Food
8.7Crew
Airline reviews

All good the seats a little tight and no I pad screen

10.0 ExcellentAnonymous, Jul 2025YYZ - RSW
Read more Porter Airlines reviews

All good the seats a little tight and no I pad screen

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

Our flight was cancelled at the last minute for maintenance reasons and we were rebooked on a late flight when we purposefully booked our flight to be home early due to work.

Seemed like an old plane. Very noisy. The seat cushions were so old that the metal bracing of the seats were poking through. There was plenty of leg room though.

Flight was delayed over 2 hours, then landed at a different airport!

The whole experience from check in to deboarding was fantastic.

Just an evening before they canceled my ticket and offered me ticket costing 3 x times more than. I will not fall prey to these scams,Will never book through kayak now. Such a bad experience.

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

Great! Personable crew. I love that they pour complimentary beer and wine.

I love the 2 seats per row. More room. The crew were excellent.

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

Information on your arrival and departure airports

Montreal (YUL)
Midway (MDW)

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