MDW - YUL

$138 Find Cheap Flights from Chicago Midway Airport to Montreal

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Montreal departing on 12/19. 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, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Montreal Pierre Elliott Trudeau Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Montreal, 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 Chicago to Montreal, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Midway to Montreal (MDW-YUL)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Montreal 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 Midway to Montreal

Tue, Jan 27 - Thu, Jan 29
Porter Airlines Logo
11:00 am - 4:30 pmMDW-YUL
4h 30m1 stop
Porter Airlines Logo
6:45 am - 10:05 amYUL-MDW
4h 20m1 stop
$260Porter Airlines
Find Deal
Sat, Jan 10 - Mon, Jan 12
Porter Airlines Logo
12:45 pm - 6:45 pmMDW-YUL
5h 00m1 stop
Porter Airlines Logo
6:45 am - 10:05 amYUL-MDW
4h 20m1 stop
$277Porter Airlines
Find Deal
Sat, Dec 20 - Tue, Dec 23
Porter Airlines Logo
4:15 pm - 10:45 pmMDW-YUL
5h 30m1 stop
Porter Airlines Logo
11:25 am - 3:20 pmYUL-MDW
4h 55m1 stop
$293Porter Airlines
Find Deal
Thu, Dec 11 - Fri, Dec 12
Porter Airlines Logo
11:00 am - 5:45 pmMDW-YUL
5h 45m1 stop
Porter Airlines Logo
6:45 am - 10:05 amYUL-MDW
4h 20m1 stop
$294Porter Airlines
Find Deal
Fri, Dec 5 - Tue, Dec 9
Multiple Airlines Logo
3:52 pm - 7:44 pmMDW-YUL
26h 52m2 stops
Multiple Airlines Logo
6:45 am - 10:05 amYUL-MDW
4h 20m1 stop
$295Multiple Airlines
Find Deal
Thu, Dec 18 - Sun, Dec 21
Porter Airlines Logo
11:00 am - 5:45 pmMDW-YUL
5h 45m1 stop
Porter Airlines Logo
11:25 am - 3:20 pmYUL-MDW
4h 55m1 stop
$296Porter Airlines
Find Deal
Mon, Dec 8 - Thu, Dec 11
Porter Airlines Logo
11:00 am - 4:30 pmMDW-YUL
4h 30m1 stop
Porter Airlines Logo
6:45 am - 10:05 amYUL-MDW
4h 20m1 stop
$299Porter Airlines
Find Deal
Tue, Nov 18 - Sat, Nov 22
Multiple Airlines Logo
6:26 pm - 1:00 pmMDW-YUL
17h 34m2 stops
Multiple Airlines Logo
8:55 am - 11:50 amYUL-MDW
3h 55m1 stop
$327Multiple Airlines
Find Deal
Tue, Dec 9 - Thu, Dec 11
Delta Logo
5:29 pm - 11:59 pmMDW-YUL
5h 30m1 stop
Delta Logo
6:30 pm - 11:47 pmYUL-MDW
6h 17m1 stop
$363Delta
Find Deal
Sun, Nov 23 - Sun, Nov 30
WestJet Logo
10:47 am - 5:21 pmMDW-YUL
5h 34m1 stop
WestJet Logo
6:26 pm - 9:52 amYUL-MDW
16h 26m1 stop
$381WestJet
Find Deal

Everything you should know

Top airlines
Porter Airlines
Cheapest • from $260 (round-trip)
Porter Airlines
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Cheapest round-trip
$260
Porter Airlines
Tue 1/27Thu 1/29
MDW - YUL • 1 stop
Cheapest one-way
$138
Porter Airlines
Fri 12/19
MDW - YUL • 1 stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Montreal!
Booking Insights

KAYAK's insights & trends for Midway to Montreal flights

Get data-powered insights and trends into flights from Midway to Montreal 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 Chicago Midway Airport to Montreal?

The average price of all round-trip flights from Chicago Midway Airport to Montreal Pierre Elliott Trudeau Intl Airport clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago Midway Airport to Montreal, look for departures on Saturdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Montreal, Friday is the cheapest day to fly and Sunday is the most expensive.

Good to know

Cheapest flight$138
Flight from Chicago Midway Airport to Montreal

When to book flights from Midway to Montreal

Are your dates flexible? Find out the best times to travel from Midway to Montreal 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 Chicago Midway Airport to Montreal flights

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

    In the last 3 days, the lowest price for a flight from Chicago Midway Airport to Montreal Pierre Elliott Trudeau Intl Airport was $138 for a one-way ticket and $260 for a round-trip.

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

    Yes, you’ll need a passport to travel to Montreal from Chicago Midway Airport.

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

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

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

    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 Chicago Midway Airport to Montreal.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Montreal from Chicago Midway Airport 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 Chicago Midway Airport to Montreal?

    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 Montreal with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and YUL 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 Chicago Midway Airport to Montreal?

    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 Montreal from Chicago Midway Airport 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 Midway to Montreal

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Montreal. 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 Midway to Montreal? 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 384 reviews
7.0Entertainment
8.2Boarding
7.6Food
8.6Crew
8.0Comfort
Airline reviews

I like it, but the food isn't good. They need to offer more simple things. This bowls that have so many things your don't know what your are eating. The milenials like it, no the rest. And last but not least, they allowed somebody have a huge dog, vey agressive and fidgety in the flight. That's horrible. No animals should be allowed inside the airplane, what about allergies, etc

8.0 ExcellentPilar, Oct 2025FLL - YOW
Read more Porter Airlines reviews

I like it, but the food isn't good. They need to offer more simple things. This bowls that have so many things your don't know what your are eating. The milenials like it, no the rest. And last but not least, they allowed somebody have a huge dog, vey agressive and fidgety in the flight. That's horrible. No animals should be allowed inside the airplane, what about allergies, etc

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

The flight was half empty yet they charged me $50 for a basic carry on! I saw how passengers of different colors were treated differently.

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

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

Three hours on the tarmac with almost zero communication from the cockpit. Not when offered a water in the interim. In my 67 years of flying all over the world the worst experience ever. The plane was half empty, however had to pay for seats to sit next to my girlfriend. Extra to take a carry on. I would never fly Porter again even for free.

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

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.