MDW - YUL

$73 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 6/7. 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
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Everything you should know

Cheapest round-trip
$257
Porter Airlines
Wed 5/27Mon 6/1
MDW - YUL • 1 stop
Cheapest one-way
$73
Porter Airlines
Sun 6/7
MDW - YUL • 1 stop
Top airlines
Cheapest • from $257 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Midway and Montreal. You'll need at least 1 connection.
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We hope you love your trip to Montreal!
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

Wed, May 27 - Mon, Jun 1
Porter Airlines Logo
10:30 am - 8:10 pm
MDW
-
YUL
8h 40m
1 stop
Porter Airlines Logo
6:30 am - 2:35 pm
YUL
-
MDW
9h 05m
1 stop
$257Porter Airlines
Fri, Jun 5 - Thu, Jun 25
Porter Airlines Logo
10:15 am - 5:15 pm
MDW
-
YUL
6h 00m
1 stop
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
$258Porter Airlines
Fri, Jun 5 - Sun, Jun 7
Porter Airlines Logo
10:15 am - 5:15 pm
MDW
-
YUL
6h 00m
1 stop
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
$259Porter Airlines
Thu, Jun 4 - Mon, Jun 8
Porter Airlines Logo
10:15 am - 8:10 pm
MDW
-
YUL
8h 55m
1 stop
Porter Airlines Logo
6:30 am - 2:35 pm
YUL
-
MDW
9h 05m
1 stop
$265Porter Airlines
Fri, Jun 5 - Thu, Jun 11
Porter Airlines Logo
10:15 am - 5:15 pm
MDW
-
YUL
6h 00m
1 stop
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
$272Porter Airlines
Fri, Jun 5 - Wed, Jun 10
Porter Airlines Logo
10:15 am - 5:15 pm
MDW
-
YUL
6h 00m
1 stop
Porter Airlines Logo
6:30 am - 9:35 am
YUL
-
MDW
4h 05m
1 stop
$274Porter Airlines
Fri, Jun 5 - Sun, Jun 7
Porter Airlines Logo
10:15 am - 5:15 pm
MDW
-
YUL
6h 00m
1 stop
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
$276Porter Airlines
Mon, Jun 1 - Thu, Jun 11
Porter Airlines Logo
10:15 am - 8:10 pm
MDW
-
YUL
8h 55m
1 stop
Porter Airlines Logo
6:30 am - 2:35 pm
YUL
-
MDW
9h 05m
1 stop
$283Porter Airlines
Fri, Jun 5 - Mon, Jun 8
Porter Airlines Logo
10:15 am - 5:15 pm
MDW
-
YUL
6h 00m
1 stop
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
$290Porter Airlines
Fri, Jun 5 - Mon, Jun 8
Porter Airlines Logo
10:15 am - 5:15 pm
MDW
-
YUL
6h 00m
1 stop
Porter Airlines Logo
10:35 am - 2:35 pm
YUL
-
MDW
5h 00m
1 stop
$292Porter Airlines
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.

Which airlines provide the cheapest flights from Chicago Midway Airport to Montreal?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Chicago Midway Airport to Montreal were found on Porter Airlines ($257) and KLM ($355).

Good to know

Cheapest flight$73
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 $73 for a one-way ticket and $257 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 435 reviews
7.6Food
8.0Comfort
8.2Boarding
7.0Entertainment
8.6Crew
Airline reviews

A few improvements: 1. No signages at the airport that the porter airline was a codeshare and i could check-in at American counter. 2. Crew at the gate said they couldn't change my reward to Alaska - despite that being done previously 3. Despite there being many open seats, i was assigned a seat at the very back near lavatory, last row. Fortunately, the pilot wanted more people moved up so the flight attendants moved me up. It seemed very odd to have been stuck in last row with very few people nearby..

6.0 GoodHarsh, Apr 2026
JFK - YYZ
Read more Porter Airlines reviews

A few improvements: 1. No signages at the airport that the porter airline was a codeshare and i could check-in at American counter. 2. Crew at the gate said they couldn't change my reward to Alaska - despite that being done previously 3. Despite there being many open seats, i was assigned a seat at the very back near lavatory, last row. Fortunately, the pilot wanted more people moved up so the flight attendants moved me up. It seemed very odd to have been stuck in last row with very few people nearby..

I didn’t receive any help when they messed up and wasn’t honest and the supervisor did absolutely nothing to help me so I had to buy another ticket at $537

There was No Flight. Both Kayak and Porter refused to honor my booking. I was asked for an additional 1,300 $ CAD to keep the flight. After several emails to both Kayak and Porter I was ignored. I had to cancel my March spring break plans, dog kennel and hotel. I had to re-book another vacation to Nassau in January w Expedia. I had to re-book a new vacation for spring break. Porter and Kayak both blamed each other and would not work together to fix this. Not cool.

Even tho the flight was a bit delayed the team was apologetic. Everyone was friendly and efficient.

The flight was a little delayed but check in was easy and boarding was quick. Luggage was quickly available and everything worked great.

The Flight took off 2hrs late because there was no pilot showing up when the flight was ready to board.. Though the cabin crew was present and had prepared the plane, the FO turned around after 15 min and went away. A crew to fly the plane finally arrived over an hour later and we were able to board 1h30 min later than planned time... until everything was loaded, we left 2h late from the gate. This was a small plane, so don't expect any Entertainment... Wi-Fi access on board would work, but took an awful amount of time to figure out and get it work (I'm an IT person). Flying as VIPorter customer, I was expecting at least some warm meal, but everything served was just cold.. except the coffee maybe. Even in so-called VIPorter seats, space is cramped and trays are so tiny, you can barely setup your food. Flight caught up during the coast-to-coast crossing and was able to recoup about 45 min from the delay.. still arrived very late in Vancouver and had to wait a long time to get our registered bags. Let's see how the return flight will be in a few days..

The flight booking code given by Kayak was not the correct one used by the airline. I had to call to get the correct one. It was never sent to me. Totally unacceptable!

Due to a known technical error that Porter has not fixed in over a year, I was unable to check in the children on my reservation online and had to do it at the airport. Upon check in, there were no seats together, which was an issue as we had young children. The gate agent did manage to seat us together by moving other passengers, which was appreciated, but the other passengers were never informed, leading to confusion and delay upon boarding. The flight was over an hour late; no explanation or apology was ever issued. The bags on Porter take a long time to arrive--over half an hour at Hamilton on my inbound flight, and not much better on my return to Edmonton.

Much roomer than air Canada! Great flight for the price. No complaints

On my e-boarding pass it shows free wifi, yet the plane I was on didn’t have wifi. Please remove false advertising from your website and boarding passes

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

Information on your arrival and departure airports