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YUL - MDW

C$ 163 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 7/7. 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

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 Flight Deals 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.

Recent round-trip flight deals from Montreal to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Montreal to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
Choose your dates
Porter Airlines Logo
1:10 p.m. - 4:24 p.m.YUL-MDW
4h 14m1 stop
Porter Airlines Logo
9:40 a.m. - 4:00 p.m.MDW-YUL
5h 20m1 stop
C$ 251Porter Airlines
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Thu, 22 May - Mon, 26 May
Porter Airlines Logo
1:10 p.m. - 4:24 p.m.YUL-MDW
4h 14m1 stop
Porter Airlines Logo
9:40 a.m. - 4:00 p.m.MDW-YUL
5h 20m1 stop
C$ 252Porter Airlines
Find Deal
Tue, 20 May - Thu, 22 May
Porter Airlines Logo
10:45 a.m. - 4:24 p.m.YUL-MDW
6h 39m1 stop
Porter Airlines Logo
9:40 a.m. - 4:00 p.m.MDW-YUL
5h 20m1 stop
C$ 256Porter Airlines
Find Deal
Thu, 3 Jul - Sun, 6 Jul
Porter Airlines Logo
1:10 p.m. - 4:24 p.m.YUL-MDW
4h 14m1 stop
Porter Airlines Logo
9:40 a.m. - 4:00 p.m.MDW-YUL
5h 20m1 stop
C$ 258Porter Airlines
Find Deal
Thu, 29 May - Thu, 5 Jun
Delta Logo
7:00 a.m. - 3:20 p.m.YUL-MDW
9h 20m1 stop
Delta Logo
12:48 p.m. - 11:54 p.m.MDW-YUL
10h 06m1 stop
C$ 349Delta
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Sat, 31 May - Thu, 5 Jun
Delta Logo
6:00 a.m. - 12:32 p.m.YUL-MDW
7h 32m1 stop
Delta Logo
6:00 a.m. - 5:04 p.m.MDW-YUL
10h 04m1 stop
C$ 352Delta
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Fri, 3 Oct - Wed, 8 Oct
Logo
7:00 a.m. - 9:14 p.m.YUL-MDW
15h 14m1 stop
Logo
9:40 a.m. - 4:00 p.m.MDW-YUL
5h 20m1 stop
C$ 397
Find Deal
Sat, 17 May - Sun, 25 May
Logo
1:10 p.m. - 4:24 p.m.YUL-MDW
4h 14m1 stop
Logo
12:48 p.m. - 12:37 a.m.MDW-YUL
10h 49m2 stops
C$ 414
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Thu, 29 May - Wed, 4 Jun
WestJet Logo
6:10 a.m. - 1:15 p.m.YUL-MDW
8h 05m1 stop
WestJet Logo
2:00 p.m. - 11:18 p.m.MDW-YUL
8h 18m1 stop
C$ 471WestJet
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Sat, 31 May - Sat, 6 Sep
WestJet Logo
6:45 a.m. - 9:14 p.m.YUL-MDW
15h 29m2 stops
WestJet Logo
9:20 a.m. - 11:19 p.m.MDW-YUL
12h 59m1 stop
C$ 474WestJet
Find Deal
Sat, 17 May - Sun, 25 May

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 May, where tickets cost C$ 353 (return) on average. On the other hand, the most expensive months are October and March, where the average cost of round-trip tickets is C$ 597 and C$ 504 respectively.
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Good to know

Low season

March

High season

December

Cheapest flight

C$ 163
Best time to beat the crowds but there is an average 16% 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$ 118 for a one-way ticket and C$ 181 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.

See more FAQs

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 285 reviews
7.6Food
8.8Crew
8.2Boarding
7.0Entertainment
8.1Comfort
Airline reviews

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

10.0 ExcellentAnonymous, Apr 2025YHZ - YOW
Read more Porter Airlines reviews

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

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.

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

Information on your arrival and departure airports

Midway (MDW)
Montreal (YUL)

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