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Find First Class Flights to Chicago Midway Airport

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Sun 19/5
Sun 26/5

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 44m
  • 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 Endeavor Airlines, with an overall rating of 8.8.

See more FAQs

Top 5 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
DeltaOverall score based on 11094 reviews
7.5food
8.6crew
7.9comfort
8.2boarding
8.0entertainment
Airline reviews

Seat back monitors and outlets were dead and not working.

8.0 ExcellentCarl, Apr. 2024JFK - FLL
Read more about Delta reviews

Seat back monitors and outlets were dead and not working.

Everything was great except for the seat. The backrest would not stay in the upright position.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

Flight delayed about 2 hrs so it made it a VERY late night

It was a crowded flight. They did the best they could.

Super good crew... food was pretty awful- overall Delta is my favorite carrier- takes off on time, good boarding process etc.

I love flying DELTA it's my favorite airline to fly I love the staff the flight attendants and most importantly the safe flights that the pilots bring every time!!!! period!! My experience has been beautiful every time....I hope the good standards will always be kept

Service was good for such a short flight. Small plane but smooth flight.

Boarding was a little confusing as many folks were trying to get on through priority boarding instead of general. Everything else was excellent.

Worst flight in my life. Only was scheduled for a 45 min flight to get our connection flight. It was late by 40 minutes and we missed our connection. Delta was totally useless trying to help and unable to get my family on the next flight because they overbooked it Thus had to get a hotel at my expense and lost a day at Disney as a result. Cost me about a $1000 if you add 2 hotels meals shuttles etc to get thru the day Awful customer service by Delta in Detroit totally useless people

The flight was delayed for 2 hrs. Because they didn’t have a crew to fly. And it is not a first time for klm to do that. Last time they cancelled my filght and rebooked me 3 days later. Not reliable airline

We left one hour late because of technical difficulties. The economy comfort seats are great for the price. The crew was mediocre, they do not provide a pleasant experience, they just deliver food and drinks and give orders, not very amicable, no service and hospitality focus.

Booked connecting flights with KlM. My serving flight was the furthest part of the airport. On arrival in Zurich. My two cases arrived but only one carry on belong to my son. His three suitcase didn't arrive. After enquiring we discovered they were still in Amsterdam. We landed at 11.12. We eventually left the airport just after one.

Seats are fair enough for medium tall people. Good food all the trip. Fight attendances are warm

no issues at all... Kudos to the food. This time was really really good

The food was ok. The crew seemed like they were cranky. I had one guy get mad at me for passing in between the storage area to get to the other toilet. I can understand if it's not allowed but reprimanding me like I'm a student saying "This is the last time!" was not appropriate. During my meal time, there was a French family around me. No problems there but when we usually have meals, they are supposed to put their chair in the upright position. These people did not do it and the steward did not tell them to raise their seat in the upright position. However, I was told to do so! So, me and another person next to me had to eat with the monitor almost touching our faces. Furthermore, a lady in front of me was putting her feet up and preventing another elder passenger from putting her seat back. To make it worse, she was continuously hitting her back into her seat, shaking my monitor while I was watching a movie. A crew member did speak to her about it but then she accused me of pushing her seat forward! The crew member gave me a death stare and told me to stop pushing the seat forward. I did not even touch her seat at all, if I did, she would know it. Her boyfriend also stood up and tried to push her seat even further past the maximum decline to no avail. None of these people were reprimanded but the steward, some bald guy, was extremely friendly with them and did not even try to instruct them to do anything until it was time to land. I resisted the urge to really argue with them because I would have obviously been seen as the aggressor (I have no idea why). I hardly said anything on this flight except "more wine please" and "sorry" if I bumped into someone accidentally. Overall, it was an annoying flight and I had to resist the urge to yell at the steward and the people he was overly friendly with. The happiest moment of this flight was leaving it.

One of their staff was so rude with discriminative. Such a reputed airline shouldn't hire such kind of arrogant attendants.

Amazing KLM service and brilliant economy comfort seats. Well worth the extra.

The boarding was one of the worst I’ve ever experienced. The fault lays on Ohare Airport and not so much the airline. The waiting area by the gate was the size to accommodate a regional flight for 20-30 people and right next to a busy walkway. When you cramped nearly 300 passengers into that space is was unbearable.

Well, in my case; the flight was delayed 1 hour, we have to wait in the plane to get green light. And the plane (probably because was a short trip) did not have entertainment or WiFi. No a good experience.

Boarding - It is unclear where the line for the group are given the signs. A solution would be a diagonal arrow pointing to the lane in which the lane for boarding of a given zone should form. As it is now, you are guessing which side of the pole the "zone 3" sign is telling you to form the line. Inflight Entertainment - The Spanish subtitles function didn't work for movie watching (in fact, all subtitles didn't work), so was difficult to follow along and I watched the movie in silence without words.

An hour-long wait to check in, 90 minutes for luggage to come out, lost luggage, chaotic operations

No everybody brings the proper equipment to enjoy the plane entertainment. Then I was not able to enjoy it.

Pros: "I like the service ,the food in thos fliggt back. Excelent"
Cons: "Better rules for people who put the seat back while we eating ,some crewmembee could say something"
Pros: "Crew friendlynesd"
Cons: "Paying a little more attention to the seating. Not everyone was socially distanced. Seat rows were unequally distributed: some were all full others were too empty."
Pros: "Seat was okay, but I thought we weren't doing center seats because of Covid risk. That plane was packed tight."
Cons: "They made me store my bag, because I had a guitar which has always been allowed as a carry on. Its a fragile instrument, and has always been allowed as a carry on."
Pros: "Seats are comfortable. Compared to other flights there is more leg room. Flight attendants where friendly."
Cons: "The flight was late on arrival, so there was more time spent in the airport. Due to this, we were right behind another flight that landed before us. Customs will only allow one plane to disembark, so we waited to get off the plan for over 30 minutes. This was the only bad experience with the trip."
Pros: "The crew was attentive."
Cons: "Check in process was super slow. It took an hour and a half. Check in process needs to be made more efficient. Also, plane took off an hour and 20 minutes later than originally planned. Therefore, we landed an hour later than expected."
Pros: "Movies and shows. Blankets. Prompt staff on plane. Snack options."
Cons: "Ticket counter was stubborn to release our boarding passes despite having already checked in online. Saying we were “too late”. The kiosk would not release our boarding passes either. Yet, we breezed right through security to the gate and we’re first to board the plane having had to actually wait awhile before boarding. The ticket counter person unnecessarily made us wait even longer when we were already running late due to having spent 11 hours in the hospital day prior from E. coli. The boarding process was also sloppy. Three different attendants asked to see our passports. Why did everyone need to verify us? We were asked very silly and seemingly unnecessary questions before boarding further slowing the process. We were asked before boarding if we had checked a bag, not sure what difference that made."
Pros: "The flight was delay about an hour, on board. The crew was great. No entertainment on board. Good complimentary bar."
Cons: "Being on time"

I wish that seats closer to the front of the plan were available, but when I booked the flight the seats were VERY expensive so I did not book seats at that time. The day before flying only seats at the back of the plane were available. It takes so long to board the plane and empty the plane on arrival due to SO many roller bags.

Crew was rude.didn’t even say hi or welcome to board

Good flight. No I’m seat entertainment. But my phone worked just fine on the west jet app.

Nothing special. Unacceptable wait for baggage on arriving in Calgary

Departure delay on a late night flight. Made us even later. Tired but got home.

I had planned to watch the Westjet entertainment for the entire flight however, because the seat mounted outlets in our row did not work.

Westjet forced me to put my carry-on baggage in check-in probably because I was assigned seat 23A (the last row seat), which had no cabin space, which is unfair. I wanted to carry on my luggage so that I don't have to wait at the airport for my luggage. Also, because there was no cabin space, I was forced to keep my laptop bag under the seat, which I didn't want to as I was carrying 2 laptops and charger. The airline should basically tell people that if you are assigned a last row seat, then you are not allowed a cabin baggage or a personal item.

Not a bad flight but our priority tagged luggage was the very last to come down the carousel.

Plane had a flat tire, delayed boarding and takeoff but one in the air, smooth. Make sure you have downloaded the WJ app before you leave. When on board, you can watch movies or TV shows offered on the app, it passed the time very quickly.

Easy processing, flight time was quick and staff was professional and kind.

First time with Porter and I can say this is best airline company in Canada. Great service, free WiFi, free snack and drinks (including beer and wine). Seats were super comfy on the Embraer jet and I appreciated the folding try table too. Staff were excellent both legs of the trip.

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

Great. Porter is very efficient, welcoming, and organized. I fly Porter often.

Check in was slow because of passenger ahead in Reserve line. Seats were somewhat uncomfortable.

First time with Porter. Amazing experience overall, will be my airline of choice in North America whenever possible. Liked the quality of food and how it was served but one suggestion- a hot meal on the longer flights, perhaps?

Delayed by 2.5 hours. This happened previously on my flight from YOW to YVR on Dec. 26.2023. This is a terrible airline. The reason was there was lack of ground crew. This is a known event. AVOID PORTER AIRLINES IF YOU CAN. There is a reason half the plane was empty.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10 Tips for people flying porter from Boston. The airline doesn’t have inflight entertainment No TV No WIFI. Bring your entertainment with you.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10

Wasn’t on the flight- again. Bad weather in Halifax and I was in an accident. What a poor experience to have to pay for all this flight and not be on it

I didn’t make my flight due to poor weather and I had an accident driving there. I tried to get my money back or even credit and nothing. I have an entire flight both to Florida and back that I paid for and no one will give me any money back. I know this isn’t just Porter and it’s 3rd party- however airlines should allow these companies to take money for things they don’t get. I’m so upset. Who can afford a full flight they never take?

Book first class plane tickets to Chicago Midway Airport

Recent round-trip first class deals

 
We’ve provided our cheapest round-trip first class flights to Chicago found on KAYAK in the last 72 hours.
25/5Sat
2 stopsDelta
11h 03mYUL-MDW
27/5Mon
1 stopDelta
8h 47mMDW-YUL
C$ 1,233
23/5Thu
1 stopDelta
8h 21mYUL-MDW
26/5Sun
2 stopsDelta
10h 43mMDW-YUL
C$ 1,449
23/5Thu
2 stopsDelta
8h 06mYUL-MDW
25/5Sat
1 stopDelta
5h 31mMDW-YUL
C$ 1,468
11/6Tue
2 stopsDelta
11h 04mYUL-MDW
15/6Sat
1 stopDelta
4h 19mMDW-YUL
C$ 1,545
20/6Thu
2 stopsDelta
8h 04mYUL-MDW
24/6Mon
1 stopDelta
4h 19mMDW-YUL
C$ 1,548
21/5Tue
2 stopsDelta
12h 55mYVR-MDW
21/6Fri
2 stopsDelta
10h 18mMDW-YVR
C$ 2,151

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Recent one-way first class deals

 
Only flying one-way? Below are some of the best deals for one-way first class flights to Chicago found on KAYAK in the last 72 hours.
23/5Thu
1 stopDelta
8h 21mYUL-MDW
C$ 475
27/9Fri
1 stopDelta
6h 18mYYC-MDW
C$ 736
26/9Thu
1 stopDelta
10h 28mYYC-MDW
C$ 779
23/5Thu
2 stopsDelta
12h 55mYVR-MDW
C$ 866
23/5Thu
2 stopsDelta
8h 06mYUL-MDW
C$ 967
23/5Thu
1 stopDelta
10h 36mYVR-MDW
C$ 1,463

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Flights to Chicago Midway Airport

Destination:

Chicago Midway (MDW)United States

Return flight deals:

Chicago Midway - Canada

Cabin classes:

C$ 546
C$ 292

Browse origins: