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YUL - MDW

$120 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 Midway departing on 6/4. 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

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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Cheap Flights from Montreal to Midway

 
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.

Recent round-trip flight deals from Montreal to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Montreal to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Porter Airlines Logo
1:10 pm - 4:24 pmYUL-MDW
4h 14m1 stop
Porter Airlines Logo
9:40 am - 4:00 pmMDW-YUL
5h 20m1 stop
$179Porter Airlines
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Thu, May 22 - Mon, May 26
Porter Airlines Logo
1:10 pm - 4:24 pmYUL-MDW
4h 14m1 stop
Porter Airlines Logo
5:20 pm - 10:15 pmMDW-YUL
3h 55m1 stop
$181Porter Airlines
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Tue, May 20 - Tue, May 27
Porter Airlines Logo
10:45 am - 4:24 pmYUL-MDW
6h 39m1 stop
Porter Airlines Logo
9:40 am - 4:00 pmMDW-YUL
5h 20m1 stop
$185Porter Airlines
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Thu, Jul 3 - Sun, Jul 6
Porter Airlines Logo
1:10 pm - 4:24 pmYUL-MDW
4h 14m1 stop
Porter Airlines Logo
9:40 am - 4:00 pmMDW-YUL
5h 20m1 stop
$186Porter Airlines
Find Deal
Thu, Jul 3 - Sun, Jul 6
Delta Logo
6:00 am - 8:40 amYUL-MDW
3h 40m1 stop
Delta Logo
4:15 pm - 11:54 pmMDW-YUL
6h 39m1 stop
$238Delta
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Thu, Jun 5 - Fri, Jun 6
Delta Logo
7:00 am - 3:20 pmYUL-MDW
9h 20m1 stop
Delta Logo
12:48 pm - 11:54 pmMDW-YUL
10h 06m1 stop
$252Delta
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Sat, May 31 - Thu, Jun 5
Logo
6:45 am - 4:54 pmYUL-MDW
11h 09m1 stop
Logo
9:40 am - 4:00 pmMDW-YUL
5h 20m1 stop
$257
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Sun, Jun 8 - Wed, Jun 11
Logo
1:10 pm - 4:24 pmYUL-MDW
4h 14m1 stop
Logo
12:48 pm - 12:37 amMDW-YUL
10h 49m2 stops
$289
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Thu, May 22 - Thu, May 29
WestJet Logo
6:10 am - 1:15 pmYUL-MDW
8h 05m1 stop
WestJet Logo
2:00 pm - 11:18 pmMDW-YUL
8h 18m1 stop
$340WestJet
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Sat, May 31 - Sat, Sep 6
WestJet Logo
6:15 am - 1:15 pmYUL-MDW
8h 00m1 stop
WestJet Logo
12:48 pm - 12:37 amMDW-YUL
10h 49m2 stops
$342WestJet
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Tue, May 13 - Wed, May 14

KAYAK's insights & trends for Montreal to Midway flights

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

The average price of all round-trip flights from Montreal Pierre Elliott Trudeau Intl Airport to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.
When flying from Montreal to Chicago Midway Airport, you should consider leaving on a Friday and avoid Sundays if you are looking for the best rates. For your return to Montreal, you’ll find the best rates on Saturdays and the most expensive ones on Mondays.

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 May, where tickets cost $255 (return) on average. On the other hand, the most expensive months are October and March, where the average cost of round-trip tickets is $431 and $364 respectively.
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Good to know

Low season

March

High season

December

Cheapest flight

$120
Best time to beat the crowds but there is an average 16% increase in price.
Most popular time to fly with an average 4% increase in price.
Flight from Montreal to Chicago Midway Airport

When to book flights from Montreal to Midway

Are your dates flexible? Find out the best times to travel from Montreal to Midway 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 $120 for a one-way ticket and $179 for a round-trip.

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

    A passport is required to fly from Montreal to Chicago Midway Airport.

  • 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 travelers 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. Booking your flights between Montreal and MDW 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 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 Midway

 
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 Midway? 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 284 reviews
8.2Boarding
7.0Entertainment
7.6Food
8.8Crew
8.1Comfort
Airline reviews

It was amazing although they did bump us up to the front which gave us more leg room and a meal. The service was great! The staff were friendly. :)

10.0 ExcellentDiane, Apr 2025YYZ - TPA
Read more Porter Airlines reviews

It was amazing although they did bump us up to the front which gave us more leg room and a meal. The service was great! The staff were friendly. :)

Overall very good... staff were friendly and helpful. boarding was good for the most part, but a little hard to get our carry-on bags on there.... I think people should be directed to keep their coats and small bags with them until all the carry-ons are loaded, and then, if there is space, they can put their small bags and coats up top.. makes it much easier to put baggage up. i loved the internet feature, but the entertainment was not there unless you have your own Netflix or similar platform. My chair did not recline, which was very annoying, and the arms won't go up near the isle, which makes it tough to get in and out of the seat.

Staff were excellant. Only snacks served. Some turbulence so we were offered Free beer or wine.

The staff is always great. Just the fact that our flight was the only one delayed from Halifax when all other carries were still flying. It happen a year ago out of Toronto as well. All others were flying but our flight got cancelled 1 hr before the time of departure.

The only issue had when i mentioned about comfort was the man beside me was on the larger side and took about 1/3 of my seat where i was pressed against the wall/window of the plane for the trip.

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!

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

Information on your arrival and departure airports

Midway (MDW)
Montreal (YUL)

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