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Find First Class Flights to Chicago Midway Airport

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Cheap First Class Flight Deals to Chicago Midway Airport

 
These are the cheapest deals for flights from Canada to Chicago Midway Airport currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. 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 first class round-trip flight deals to Chicago Midway Airport

Fri, 3 Oct - Sun, 5 Oct
Delta Logo
6:30 a.m. - 8:40 a.m.YYZ-MDW
3h 10m1 stop
Delta Logo
9:35 a.m. - 5:23 p.m.MDW-YYZ
6h 48m1 stop
C$ 794Delta
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Sun, 12 Oct - Sun, 19 Oct
Delta Logo
6:15 a.m. - 8:40 a.m.YYZ-MDW
3h 25m1 stop
Delta Logo
6:23 p.m. - 10:55 p.m.MDW-YYZ
3h 32m1 stop
C$ 799Delta
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Sat, 15 Nov - Sun, 23 Nov
Delta Logo
6:45 a.m. - 6:08 p.m.YUL-MDW
12h 23m2 stops
Delta Logo
6:00 a.m. - 5:21 p.m.MDW-YUL
10h 21m1 stop
C$ 941Delta
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Thu, 16 Oct - Sat, 18 Oct
Delta Logo
6:45 a.m. - 5:43 p.m.YUL-MDW
11h 58m2 stops
Delta Logo
6:23 p.m. - 11:14 p.m.MDW-YUL
3h 51m1 stop
C$ 1,482Delta
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Wed, 29 Oct - Wed, 5 Nov
Delta Logo
6:00 a.m. - 12:28 p.m.YUL-MDW
7h 28m1 stop
Delta Logo
9:35 a.m. - 6:40 p.m.MDW-YUL
8h 05m2 stops
C$ 1,586Delta
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Mon, 20 Oct - Wed, 22 Oct
Delta Logo
7:00 a.m. - 4:09 p.m.YUL-MDW
10h 09m1 stop
Delta Logo
9:35 a.m. - 6:40 p.m.MDW-YUL
8h 05m2 stops
C$ 1,599Delta
Find Deal
Thu, 16 Oct - Sun, 19 Oct
Delta Logo
6:45 a.m. - 5:43 p.m.YUL-MDW
11h 58m2 stops
Delta Logo
6:23 p.m. - 11:14 p.m.MDW-YUL
3h 51m1 stop
C$ 1,611Delta
Find Deal
Thu, 16 Oct - Sat, 18 Oct
Delta Logo
6:45 a.m. - 5:43 p.m.YUL-MDW
11h 58m2 stops
Delta Logo
6:23 p.m. - 11:14 p.m.MDW-YUL
3h 51m1 stop
C$ 1,714Delta
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Mon, 29 Sep - Tue, 30 Sep
Delta Logo
6:00 a.m. - 8:40 a.m.YUL-MDW
3h 40m1 stop
Delta Logo
9:35 a.m. - 9:57 p.m.MDW-YUL
11h 22m2 stops
C$ 1,732Delta
Find Deal
Tue, 30 Sep - Sun, 30 Nov
Delta Logo
6:00 a.m. - 1:03 p.m.YUL-MDW
8h 03m2 stops
Delta Logo
9:32 a.m. - 3:55 p.m.MDW-YUL
5h 23m1 stop
C$ 1,748Delta
Find Deal
Useful Info

When to book first class flights to Chicago Midway Airport

Are your dates flexible? We break down the daily and monthly prices for first class flights to Chicago Midway Airport, so you can find the best time to fly.
Average price per month
To calculate monthly average prices, KAYAK takes all prices for each month over the last year for first class flights to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all the values for each month.
Flight prices as travel date approaches
To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for first class flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.

FAQs for Chicago Midway Airport first class flights

  • How long is a flight to Chicago Midway Airport?

    Flights from Toronto1h 45m
  • What is the most popular airline offering First Class flights to Chicago Midway Airport?

    Among KAYAK users, Delta is the most popular airline offering First Class seats on flights to Chicago Midway Airport.

  • Which airlines offer First Class tickets on flights to Chicago Midway Airport?

    Traveling to Chicago Midway Airport and want to offer yourself a First Class experience? Depending on the origin, the following airlines offer seats in First Class: Delta.

  • How does KAYAK find such good deals on First Class tickets to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago Midway Airport for economy class as well as First Class travelers.

  • What is the best airline for first class flights to Chicago Midway Airport?

    The highest-rated airline by KAYAK users offering first class flights to Chicago Midway Airport is Porter Airlines, with an overall rating of 7.9.

Reviews of the top 3 airlines flying to Chicago Midway Airport

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Canada to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly first class to Chicago Midway Airport? 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.
7.9
Porter AirlinesOverall score based on 363 reviews
7.9Comfort
7.6Food
8.1Boarding
8.6Crew
7.0Entertainment
Airline reviews

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.

2.0 MediocreAnonymous, Sep 2025YDF - YHZ
Read more Porter Airlines reviews

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

All good the seats a little tight and no I pad screen

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

Our flight was cancelled at the last minute for maintenance reasons and we were rebooked on a late flight when we purposefully booked our flight to be home early due to work.

Seemed like an old plane. Very noisy. The seat cushions were so old that the metal bracing of the seats were poking through. There was plenty of leg room though.

Flight was delayed over 2 hours, then landed at a different airport!

This has been the worst experience I’ve ever had. Basically, I lost my round-trip tickets because one of my last names was missing, and you didn’t allow me to correct it. I had to purchase a full ticket again. Once I get home, I will start legal proceedings against you.

The crew were polite and courteous. The Pilot did an excellent landing. It was very smooth and gentle. My only regret is that I was charged twice for my luggage . The attendant gave me no receipt . I didn't realize until I was about to board. How can this be resolved? Thank you.

Very smooth flights Toronto to Rome and return. Crews were great, food was fine but very narrow seats and limited leg room. Aisle seats on our return helped with a bit more space.

YUL AIRPORT is the worst. 1 Hr to Get out of the plane, 1 Hr To Cross the Border. 1Hr waiting to be pick up curbside. Trafic is ubeliveble.

It’s ok just the boarding point is far too far

Check in slow even though completed online check in, there was no bag drop available so had to query for 90mins as only 2 staff on desks.

Flying to a far away destination is a miracle in itself, so please take these with a grain of salt. The seats are a bit tired, and need a freshen up. The entertainment could be a bit newer, especially with all services available now. The food really is where we need help. But again, flying is a privilege, so all is good.

Not so much porter it's your site! Not good

They are a sister company with Air Transat and the two companies do not work well together. If you have any issues the two companies will blame each other and you will miss your flights. The help line does not help

Never book through a third party. Book through Air transats website. Terrible process to get help and many issues happen with them and sister companies because half the flights you book with them aren’t even through air transat.

There was a man who was very rude at boarding. On the other hand personal bag measuring box is too small compared to USA airlines,

A little better seat cushions would be appreciated. Crews were all good.

The process and flight were both smooth and trouble free

Flight delayed 3 hours, missed my connection in Atlanta. Instead of getting to Savannah at 6PM arrived after 10:00PM Middle seat, couldn't get isle or window, couldn't book my seats in advance, had to book at the gate. That's a 1st for me and I used to travel a lot

my carry-on bag was delayed and I did not receive it until the day of my return at the airport. This delay caused me significant inconvenience, as I did not have access to my personal belongings for the duration of my trip. I had expected to rely on my carry-on items, and being without them negatively impacted my travel experience.

Technology issues at the bag-check counter caused a delay, and we were unable to check out our bags, ultimately missing our flight. They offered no assistance other than telling us to book another flight out of Calgary. We arrived with plenty of time; if there hadn't been an issue with the kiosk and the length of the lines due to the technical issues, we could have made it home.

Worst check in and bag drop off experience. Staff were incredibly rude given that it’s the WestJet system that is faulty.

The staff at the airport and on the plane were wonderful I especially wanna acknowledge the staff who boarded us at the Calgary airport. The women who helped us board at the airport were incredible… they were so kind and sweet…I very happy with WestJet and I am hoping I can fly more often to Canada.

We were happy with our experience. The price for tickets was much less than Delta and we actually took off and landed a little ahead of scheduled times.

Seat back entertainment monitors would be nice. We did enjoy the In-Flight WiFi.

Everything you need to know for your flight to Chicago Midway Airport

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