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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

Wed, 23 Jul - Fri, 25 Jul
Delta Logo
12:16 p.m. - 6:40 p.m.YYZ-MDW
7h 24m1 stop
Delta Logo
1:46 p.m. - 11:10 p.m.MDW-YYZ
8h 24m1 stop
C$ 765Delta
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Tue, 15 Jul - Wed, 16 Jul
Delta Logo
6:30 a.m. - 12:29 p.m.YYZ-MDW
6h 59m1 stop
Delta Logo
1:46 p.m. - 11:10 p.m.MDW-YYZ
8h 24m1 stop
C$ 812Delta
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Tue, 23 Sep - Tue, 30 Sep
Delta Logo
12:47 p.m. - 9:36 p.m.YUL-MDW
9h 49m1 stop
Delta Logo
9:35 a.m. - 9:57 p.m.MDW-YUL
11h 22m2 stops
C$ 887Delta
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Thu, 17 Jul - Fri, 18 Jul
Delta Logo
6:00 a.m. - 8:44 a.m.YUL-MDW
3h 44m1 stop
Delta Logo
6:20 p.m. - 11:08 p.m.MDW-YUL
3h 48m1 stop
C$ 1,053Delta
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Wed, 24 Sep - Wed, 1 Oct
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$ 1,165Delta
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Mon, 14 Jul - Tue, 15 Jul
Delta Logo
6:30 a.m. - 12:29 p.m.YYZ-MDW
6h 59m1 stop
Delta Logo
6:20 p.m. - 10:58 p.m.MDW-YYZ
3h 38m1 stop
C$ 1,202Delta
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Sun, 3 Aug - Sun, 10 Aug
Delta Logo
9:25 a.m. - 5:39 p.m.YEG-MDW
7h 14m1 stop
Delta Logo
9:24 a.m. - 3:58 p.m.MDW-YEG
7h 34m1 stop
C$ 1,412Delta
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Sun, 17 Aug - Tue, 19 Aug
Delta Logo
6:00 a.m. - 12:28 p.m.YUL-MDW
7h 28m1 stop
Delta Logo
9:31 a.m. - 9:48 p.m.MDW-YUL
11h 17m2 stops
C$ 1,435Delta
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Mon, 21 Jul - Sun, 31 Aug
Delta Logo
6:00 a.m. - 12:29 p.m.YUL-MDW
7h 29m1 stop
Delta Logo
9:31 a.m. - 9:48 p.m.MDW-YUL
11h 17m2 stops
C$ 1,522Delta
Find Deal
Sat, 2 Aug - Sun, 10 Aug
Delta Logo
12:05 a.m. - 12:29 p.m.YEG-MDW
11h 24m2 stops
Delta Logo
9:24 a.m. - 3:58 p.m.MDW-YEG
7h 34m1 stop
C$ 2,032Delta
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 8.0.

Reviews of the top 4 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.
8.0
Porter AirlinesOverall score based on 298 reviews
8.7Crew
7.0Entertainment
8.2Boarding
7.7Food
8.1Comfort
Airline reviews

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

8.0 ExcellentChaim, Jul 2025YYZ - LGA
Read more Porter Airlines reviews

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

Great! Personable crew. I love that they pour complimentary beer and wine.

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

Leaving on time and having my luggage on my connecting flight

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

My flight was extremely cold. I had a jacket and a cover was left in each seat. The cover was extremely thin and I have a disability, fibromyalgia and arthrithis and AC air is the worst. I closed my vent and my husbands vent and it still was frigid. I asked the attendant if I could get another cover and she quickly almost dismissively and totally unconcerned stating, (I quote) (one per chair) and walked off so quickly that I didn't get a chance to explain to her that I literally have adisability. I didnt want to make a seen so I set on that flight for over 5 hours in pain, joints locking up and extremely uncomfortable. When my fibromyalgia flares up my joints not only ache but they will lock up also and it takes me days to get back to my regular self even though I take medication for it. I felt like it would not have hurt anyone at all for her to just give me an extra cover because I'm sure they have all types of medical issues in people that fly every day.

After all the weather issues at least they got me to my destination the next day

My flight was canceled after being rescheduled for four days canceling my trip. Kayak and everyone affiliated with it I.e the airlines, and just fly have been excruciating to deal with. My trip to visit family had to be canceled as there was no way to make it. I am furious at all of you.

They delayed our flight because of bad weather in NY which was completely understandable. Then they cancelled our flight and a later flight that evening. The earliest we could fly was the next morning. We ended up buying last minute tickets on another airline and made it home slightly delayed but safely that evening. Delta kept saying it was weather related but if that was the case how did we make it back on another airline? The weather in NY was cloudy but not bad.

From Atlanta to Savannah - flight connection was way to short (we weren't even late landing ) and flight was already boarding when we landed - we were told we were the last on board and so we had to gate check our bags. Once we got on the plane, there were at least seven open bag spots so that was unnecessary delay. There should be better communication between the gate agent and the crew.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

The way BCN airport handled boarding was a huge improvement over our trip to Spain from JFK. Instead of gate-mosquitos edging in before their zone was called, in BCN they had clearly marked lines for Zones 1-8 and people just lined up correctly. The flight itself was uneventful. The meal (curried chicken and rice) was one of the better meals we've had on Delta. Entertainment options were plentiful, power chargers were available in Main Cabin, and seats were decent. Flight staff were very friendly and positive throughout the 8 hour flight.

Seats were very tight especially for first leg of trip.

Not necessarily a Transat issue but it took 2 hours to go through immigration. Tried to reach out to Transat for resolution but was unable to reach an agent.

The flight was excellent, once it started, however we were delayed two hours when the first plane’s engines wouldn’t start. They found another identical plane and transferred us and our luggage in under two hours and made up almost an hour in the air.

Really low cost trip for the huge amount I paid…o paid 550 dollars just for the trip, one way trip, plus 95 for 1 luggage’s and the second 135 dollars…no blanket, not headphones for entertainment, food was served after 3 hours and 2 hours after, breakfast was served Bad, low cost company for high prices

The flight and crew were good. Departure and arrival were timely. Check-in was professional and helpful in Malaga on return trip (same on outbound trip from Toronto). The ad before ach program was punishing - specifically for the internet/data service with the content creator that was showed twice in each ad pod. It was so annoying I made an effort to forget the name and would not use the service. Provide an opportunity to fast forward or skip the darn ads once they have been initially viewed.

Extra attention to kids, thank you, we appreciate! Perfect landing

Over the wing seat at emergency exit only downside people using lavatory have no respect and wait in the space

Flight delayed any hour and couple of big gate changes

The pilot came out and chatted with the passengers. He explained why there was a slight delay. The crew was excellent. Very helpful. I had to buy meals for my whole family and they were in different seats, so the crew had to deal with that. They were very pleasant and accommodating and did a great job!

We were unable to land in Liberia. It was not the airline’s fault, but we had to be diverted to SJO.

Generally good. However. The flight left 30 mins behind schedule with no reason given.

Flight delayed, missed my pick-up had to Uber, plus missed dinner and medication, so sad!

WestJet canceled my booking, replaced it with a booking that didn't work (departing from cruise ship), and didn't offer any flights that did work. Their only option was for me to cancel and go to another airline for more money. Which I did.

Nothing to like because my inbound flight was cancelled without notification by West Jet or third party, JustFly. I couldn’t take the inbound flight due to cancellation; therefore could not take the outbound flight back.

The seats are totally uncomfortable making the flight less than pleasant. The cookies & pretzels were terrible!!!

Not the greatest experience everything was pretty mediocre. My seat was by the washroom in the aisle and was not located well as everyone past each other people were right in my seat and space.

The small prop plane was crowded and the overhead luggage storage is a smaller than on the jets. Other than that, the crew was good, the flight was on time and the landing was smooth.

There was a medical emergency that the crew handled very well. There was no “entertainment” of any sort-no movie/music/whatever. Food was typical of airlines: mediocre.

Late departure, so I missed connection in Detroit. But Delta gave me a great hotel & breakfast. Just sorry I could not get anything from my checked baggage.

Crew was friendly. Lost our luggage and told us it’d be in later in the evening of the day we returned. It was not. Still after 5 days have not received it.

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