YUL - MDW

C$ 234 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 31/3. 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 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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Everything you should know

Cheapest round-trip
C$ 259
Overall average: C$ 455
Porter Airlines
Sat 14/2Tue 17/2
YUL - MDW • 1 stop
Cheapest one-way flights
C$ 234
Porter Airlines
Tue 31/3
YUL - MDW • 1 stop
When to travel
September
Cheapest • 54% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Montreal to Chicago (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 Chicago 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

Sat, 14 Feb - Tue, 17 Feb
Porter Airlines Logo
8:55 a.m. - 11:50 a.m.
YUL
-
MDW
3h 55m1 stop
Porter Airlines Logo
11:00 a.m. - 6:45 p.m.
MDW
-
YUL
6h 45m1 stop
C$ 259Porter Airlines
Sat, 14 Feb - Tue, 17 Feb
Porter Airlines Logo
8:55 a.m. - 11:50 a.m.
YUL
-
MDW
3h 55m1 stop
Porter Airlines Logo
11:00 a.m. - 4:30 p.m.
MDW
-
YUL
4h 30m1 stop
C$ 261Porter Airlines
Wed, 18 Feb - Sun, 22 Feb
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$ 291Porter Airlines
Sun, 15 Feb - Thu, 19 Feb
Porter Airlines Logo
6:45 a.m. - 10:05 a.m.
YUL
-
MDW
4h 20m1 stop
Porter Airlines Logo
11:00 a.m. - 4:30 p.m.
MDW
-
YUL
4h 30m1 stop
C$ 292Porter Airlines
Tue, 17 Feb - Wed, 18 Feb
Delta Logo
7:00 a.m. - 11:59 a.m.
YUL
-
MDW
5h 59m1 stop
Delta Logo
1:28 p.m. - 11:10 p.m.
MDW
-
YUL
8h 42m1 stop
C$ 297Delta
Sat, 27 Dec - Mon, 23 Feb
Porter Airlines Logo
6:45 a.m. - 10:05 a.m.
YUL
-
MDW
4h 20m1 stop
Porter Airlines Logo
11:00 a.m. - 4:30 p.m.
MDW
-
YUL
4h 30m1 stop
C$ 328Porter Airlines
Sat, 27 Dec - Mon, 23 Feb
Porter Airlines Logo
6:45 a.m. - 10:05 a.m.
YUL
-
MDW
4h 20m1 stop
Porter Airlines Logo
11:00 a.m. - 6:45 p.m.
MDW
-
YUL
6h 45m1 stop
C$ 337Porter Airlines
Fri, 10 Apr - Mon, 13 Apr
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$ 348Porter Airlines
Fri, 8 May - Sun, 10 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$ 357Porter Airlines
Thu, 29 Jan - Sun, 1 Feb
Delta Logo
6:00 a.m. - 12:46 p.m.
YUL
-
MDW
7h 46m1 stop
Delta Logo
6:00 a.m. - 4:55 p.m.
MDW
-
YUL
9h 55m1 stop
C$ 359Delta
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.

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$ 212 (return) on average. On the other hand, the most expensive months are October and November, where the average cost of round-trip tickets is C$ 745 and C$ 645 respectively.

Good to know

Low seasonMarch
Cheapest flightC$ 234
Best time to beat the crowds (4% less expensive on average)
Most popular time to fly and prices are also 3% lower 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$ 234 for a one-way ticket and C$ 259 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.

  • 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.
8.0
Porter AirlinesOverall score based on 398 reviews
7.6Food
8.6Crew
7.9Comfort
8.2Boarding
7.0Entertainment
Airline reviews

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

6.0 GoodAnonymous, Dec 2025
YUL - YTZ
Read more Porter Airlines reviews

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

As a first time flyer with Porter I was happy with the service and comfort of the airline.

3.5 hr delay for a 1 hr work flight. No information as to why the delay until 20 mins before boarding.

Organization and the adjusted times but the snacks could be of a bigger portion

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

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.

The flight was fine see earlier note for the problem

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

Information on your arrival and departure airports