YUL - MDW

C$ 197 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 30/10. 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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Flight 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, 17 Oct - Mon, 20 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$ 325Porter Airlines
Find Deal
Thu, 16 Oct - Sun, 19 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$ 327Porter Airlines
Find Deal
Thu, 16 Oct - Sun, 19 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$ 328Porter Airlines
Find Deal
Wed, 15 Oct - Sun, 19 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$ 329Porter Airlines
Find Deal
Fri, 17 Oct - Mon, 20 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$ 331Porter Airlines
Find Deal
Fri, 21 Nov - Tue, 25 Nov
Porter Airlines Logo
6:45 a.m. - 10:05 a.m.YUL-MDW
4h 20m1 stop
Porter Airlines Logo
4:15 p.m. - 10:45 p.m.MDW-YUL
5h 30m1 stop
C$ 334Porter Airlines
Find Deal
Fri, 21 Nov - Mon, 24 Nov
Porter Airlines Logo
11:25 a.m. - 3:20 p.m.YUL-MDW
4h 55m1 stop
Porter Airlines Logo
11:00 a.m. - 5:45 p.m.MDW-YUL
5h 45m1 stop
C$ 335Porter Airlines
Find Deal
Sun, 12 Oct - Wed, 22 Oct
Delta Logo
6:00 a.m. - 12:28 p.m.YUL-MDW
7h 28m1 stop
Delta Logo
12:48 p.m. - 11:48 p.m.MDW-YUL
10h 00m1 stop
C$ 400Delta
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Tue, 14 Oct - Tue, 21 Oct
 Logo
4:45 p.m. - 11:25 p.m.YUL-MDW
7h 40m2 stops
 Logo
9:35 a.m. - 8:15 a.m.MDW-YUL
21h 40m1 stop
C$ 422
Find Deal
Tue, 14 Oct - Fri, 24 Oct
Delta Logo
6:00 a.m. - 12:28 p.m.YUL-MDW
7h 28m1 stop
Delta Logo
5:04 p.m. - 11:48 p.m.MDW-YUL
5h 44m1 stop
C$ 429Delta
Find Deal

Everything you should know

Top airlines
Porter Airlines
Cheapest • from C$ 325 (round-trip)
Porter Airlines
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
September
Cheapest • 32% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
C$ 325
Typical prices: C$ 399-639
Porter Airlines
Fri 17/10Mon 20/10
YUL - MDW • 1 stop
Cheapest one-way flights
C$ 197
Porter Airlines
Thu 30/10
YUL - MDW • 1 stop
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KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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.

How much is a round-trip flight from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport?

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$ 299 (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$ 597 and C$ 530 respectively.

Good to know

Low seasonMarch
Cheapest flightC$ 197
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly (3% 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$ 142 for a one-way ticket and C$ 235 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.
7.9
Porter AirlinesOverall score based on 363 reviews
8.6Crew
8.1Boarding
7.0Entertainment
7.9Comfort
7.6Food
Airline reviews

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

2.0 MediocreAnonymous, Sep 2025YDF - YHZ
Read more Porter Airlines reviews

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

This flight to St. Johns was really good. Boarding was a breeze. We left spot on time. Seats were actually pretty good. Recliner further than I expected. Three more flights to go we will see if this is the status quo for Porter.👍

I was not happy with AirfareAssist, the agency that kayak advised me would be handling my booking. I was advised by porter airlines that I had been overcharged for the Basic express , a option that I had asked airfare assist to help arrange after I realized that the basic fare I had chosen with porter did not include a carryon. At each checkin porter advised I had been overcharged for this . They advised that money would be refunded to my credit card, however, this is not likely to happen as it is not my name and credit card that appeared on the porter invoice, but that of another individual/agent. When airfare assist was arranging the basic express with porter on my behalf, they asked me to confirm that I agreed to pay $263 USD for this. I did agree, as I was advised this was needed to proceed. When I checked the invoice on the porter website and saw that it was not my name and credit card on the invoice, I was advised that this was how airfareassist processed the payment. The Porter invoice indicated a billed amount of $126USD I will not use Kayak or their designated AirfareAssist again

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

There was a 5 hour delay. Missed connection and now an almost 21 hour lay over!

The flight was fine see earlier note for the problem

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.

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

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