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Find First Class Flights to Chicago Midway Airport

1 adult
0 bags
Mon 7/1
Mon 7/8

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 Phoenix3h 34m
    Flights from Baltimore1h 54m
    Flights from Houston2h 33m
    Flights from Tampa2h 41m
    Flights from Orlando2h 46m
  • 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 Delta, with an overall rating of 8.0.

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 the United States 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.
8.1
SouthwestOverall score based on 5952 reviews
7.8Entertainment
8.7Crew
8.3Boarding
8.1Comfort
7.3Food
Airline reviews

it was a short flight, so no refreshments. Could've used some water since I was running from the end of one terminal to the end of another to catch this flight

10.0 ExcellentAnonymous, May 2024BWI - BDL
Read more about Southwest reviews

it was a short flight, so no refreshments. Could've used some water since I was running from the end of one terminal to the end of another to catch this flight

The flight took off late, which really stressed me out for 5 hours worrying about my connection. We started boarding late... not sure why. There was a long line for preboard of folks that needed assistance or were in wheelchairs and not enough attendants to help. There was one lady who seemed to hold up regular boarding bc she needed to consolidate her 3 bags into 2. I'm wondering why we all had to wait for her and not board around her. Crew on board was great! So funny, so helpful and very nice. They reassured me my connecting flight would wait... and it dead. Seems it was waiting on several connecting flights, so it took off late too. Overall a very long trip but I'm glad I didn't have to spend the night in the Baltimore airport. And why are SW terminals so far from each other. I had to haul from the end of one terminal to the end of different terminal to catch my flight.

Great no problem boarding suitcase on time for pick up

With early bird check in, I might start flying southwest again.

I stopped flying southwest a long time ago. I don’t care for their boarding process, especially when I have a family to try and seat together. The early bird check in made it so much easier. As long as you do that, it’s great.

Very helpful, convenient, nice crew members, no extra fees, helped us saving 4 hrs of travel by booking is on an earlier flight

They were great: helped us to get on an earlier flight without any fees. We saved over 4 hrs! Everything was great and affordable

Southwest never has accurate baggage claim policy information at Denver. They list one claim on the screens and invariably baggage is eventually found on another claim with zero help from staff.

I always know what to expect from Southwest - friendly crew, on time departures. I like getting free baggage. The app works great and the in-flight entertainment passes the time.

Left GEG had the first flight of the morning and couldn’t leave due to broken plane then got redirected on to another flight which then I missed my connecting flight so they rescheduled my connecting flight then that one took off 3 1/2 hours late my 4 1/2 hour day turned into a 12 1/2 hour day

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

Terrible landing. Uncomfortable seats. Great cabin crew-helpful and pleasant!

Tight fit in middle seat but OK for short flight. Crew was more interested in talking to each other than helping passengers - strickingly dissappointing. DAB is a great airport. New Haven sucks! Excellent value for the .

Avelo is definitely a budget airline and you get what you pay for. The plane was packed and the seats were not particularly comfortable. Staff was very nice and both of our flights were on time. The one thing I wish I had known was that the staff does not show up at the airport desk to check your bags until two hours before the flight. We had a 4:30 flight and had to check out of our hotel at noon. Since we have lounge passes we planned to check our bag, go through security and hang out at the lounge until we had to board. But because we could not check our bag until 2:30, when the staff showed up, we could not go through security and access the lounge. Passengers with boarding passes and carry on luggage would not have this issue. I might fly Avelo again but would only do carry on or plan to get to the airport no sooner than two hours before check in. And I would not recommend a long flight on Avelo since there is no food or entertainment and the seats are not comfortable.

No food or entertainment, but flight very comfortable and on time.

Baggage claim was barbaric at Wilmington. I realize that this is a startup airline but if they hope to grow or even survive they need to upgrade this airport. There is no automated luggage carousel and at times you are not only fighting your fellow passengers to get to your bags but also passengers coming in from other flights who cross right in front of you

No frills, i.e., no drinks or snacks. One is charged for everything. The cost really adds up. The crew and flight attendants were excellent and very pleasant.

I always walk by a pallet of Avelo branded mini bottles of water on the tarmac, but I’ve never seen them in flight. Yup, not even water offered on a 3 hour flight. No wi-fi onboard. We just watch the flight crew on their phone for 3 hours every flight. At least a mid-flight trash pickup would be great. Better than my last flight, but they only could have gone up from there. Don’t use for business or ticketed vacation like Disney… too unreliable.

You get what you pay for. The plane was dirty and the seats were awful.

Nightmare airline. Avoid Avelo. Understaffed at check-in with long, slow lines. Inexplicably had two flights and only one plane. Not weather or maintenance related apparently. One was supposed to go to Myrtle Beach and one to Orlando. I imagine someone thought it would be better to fly the available plane to Myrtle Beach and back and then go to Orlando since that round-trip was shorter. This didn’t account for the human factor of an end-of-week Orlando flight being 85% Disney passengers and putting the flight on a six-hour delay in New Haven airport… which, if you’ve been there, is tiny and has nothing to do for 50 kids excited to get to Disney. This delay was announced at the time of departure. No one realized before the time of departure there was no plane on the ground? And no one thought… hey I think the Myrtle Beach crowd might be a better one to have wait if we’re going to make a choice here (mind you the initial inbound plane was coming from Orlando and supposed to be out aircraft… they literally said let just grab this plane because it’s here to get this other group out at the last second). There is/was zero customer service desk for Avelo in HVN and there were no updates/announcements throughout the day. Plane still gets back late and we finally leave. No wi-fi on these planes, no snack or even water. I know this is budget airline, but expected at least a water after 8 hours of travel day. This should have been offered in terminal too. We land… hooray. Would you believe there is no ground crew to get the plane in to the gate… for 27 minutes. 27 minutes!!! At this point the rental car center is closing in 10 minutes, kids on the plane are crying again, and everyone is talking about how they’re never flying Avelo again. Finally get off. Bags are out at baggage claim right away (finally something right?), but they’ve stopped the carousel immediately and there is no baggage service rep. People are climbing over the carousel to get to the far side (if you’ve ever been to MCO you’ve seen it) because obviously they just stopped it immediately once all the bags were out. This airline is a dumpster fire. Icing on the cake was that while everyone was stuck in HVN, they were setting up for a celebration of their millionth passenger tomorrow. I bet 995,000 of those will never fly the airline again. Don’t fly Avelo. You’ve been warned.

Airline was the only available airline during the Southwest cancellation. It was easy to book. Lowest available fair. Convenient airports. Everything was great. Problem was, they didn’t release what gate flight was departing. The woman at the ticket booth didn’t know which terminal they were boarding and wanted me to wait in 30+ minute line versus telling me to look for flight kiosk. Burbank gate was packed. Otherwise the flight was perfect!!

It was fine. I had a lot of trouble trying to buy a seat. The Westjet website charged me and then didn’t give me my seat. I ended up keeping the seat I was assigned and hope that the charges didn’t go through.. they didn’t. But this problem with the website (trying to purchase a seat at check in) has happened a few times before. But overall the flight was good.

Terrible! Delayed three times, landed at some corner of airport, walked in bitter cold night, took a bus, bad experience

My wife and I had an uncomfortable experience with your WestJet ticket counter rep at the WestJet Priority Member ticket counter at YYC (Calgary) on May 15, 2024. I not knowing this individual’s exact name, however, in order to easily identify her, she was one (of only two at the time) ticket counter reps at your Priority members ticket counter check-in, upon our arrival around 12:15 p.m. She was a Caucasian woman with blonde hair, and wore spectacles, approximate age being probably somewhere in her 30’s or 40’s. Background: After arriving in to the West Jet terminal in Calgary (YYC), I asked a terminal employee where the West Jet check-in ticket counter was. He told me, “Column 16”. My wife and I continuing to walk through the terminal, we finally arrived at the Column 16 area, i.e. this woman’s ticket counter area, which we discovered later was the Priority Member ticket counter. However, I was simply going by the directions given to me by the previous employee, i.e. “Walk to column 16.” Standing in her line (my wife and I being the only people in her line at the time), I tried to get her attention, and I then gestured to her, motioning to her as if to ask her if I should then possibly leave the waiting line in order to then proceed to walk up to her ticket counter. She never really motioned me to come forward. I sort of had to figure this out on my own, as my wife and I then finally decided to walk forward to her station. From this point on, after I arrived at her ticket counter, never once did she ever look me in the eye. She was always looking at her computer screen, or down at the ground, as she and I occasionally exchanged conversation with one another in order for me to be able to acquire my boarding passes from her. Shortly after she began servicing us, she commented that her work section is for Priority members only. Fair enough. I did not realize this at the time. Wishing to be polite, I then mentioned to her that, if I should, I could then walk over to the regular West Jet check-in ticket counter in order to complete the check-in process. She remained quiet, never responding to this goodwill gesture of mine. She continued to work in order to print out my boarding passes, and then finally handed them to me, never at all the entire time looking at me. I told her, “Thank you.” Never once did she respond. My wife and I then walked away. Even my wife commented to me afterward that this woman absolutely never looked at us. I cannot say that this attendant was outright rude. However, she certainly was not at all warm, congenial, nor friendly. Additionally, … After getting on the plane, we then discovered that she had needlessly assigned us seats in the very last row of the plane, these being the seats adjacent to the restroom back wall, thus, unfortunately not at all reclinable. I think that the row number of this last row of seats was 30. [However, I am not sure.] How strangely awkward that we were assigned these uncomfortable row of seats when in fact the row immediately ahead of us, i.e. I think that was row 29, had two vacancies, which could have otherwise easily seated my wife and me. That is, my wife and I could have easily been assigned these more comfortable seats, which would be reclinable, and then row 30 could have otherwise had instead our two vacancies. After our flight departed, and the fasten seatbelt sign was turned off, my wife and I had hoped to “jump seats”, that is, to leave row 30 and instead sit in row 29 to utilize the reclinable seats. However, another couple apparently had the same idea as us. That is, these other two people, for whatever reason, decided to leave their previously assigned seats, and instead, seat themselves in row 29. Thus, my wife and I were stuck with these miserably cramped row 30 seats for the entire 3.5 hour flight. To reiterate, the WestJet rep we originally encountered, knowledgeable of the plane lay-out as it appeared on her computer screen, could have easily assigned us the more comfortable row 29 seats, instead of the non-reclinable row 30 seats.

It was very, very cold extremely uncomfortable almost unbearable I was sitting at the front of the cabin

Was the longest flight I have ever taken to Orlando. Not Westjet’s fault necessarily. There was a traffic issue in Orlando. We sat in the airplane for about 2 hrs before leaving Calgary on a 5 hour flight was just a little long to be stuck in the plane. Once we arrived in Orlando we were stuck in traffic on the ground for another 30min. I guess maybe the flight could be delayed so boarding would have been later so we wouldn’t have to have the discomfort of being on the plane so long.

Airport monitors did not give the gate for our flight returning Detroit to Vancouver Juice served from glass storage containers are a far more healthy alternative for people. And would also minimize the need for recycling plastic or aluminum containers

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.

I was seated next to someone so obese I had no space and was pushed against the window. I could not even put my tray down or work. My neck still hurts from that experience. They should not let that happen. Large people should have to pay for enough space.

We requested 2 wheel chairs upon arrival. On board an attendant told us to remain in our seats until everyone was off the plane. we were in row 11 and thought we would be off early. After all were off, a different attendant said we should leave, and that the chairs were gone. One was available for my friend who had just spent 9 days in hospital but I had to walk quite some distance. Eventually a cart arrived to take us the rest of the way. This was over an hour after our arrival. The staff at the terminal did their best to help us but if we had been allowed off with the other passengers, our ride home would have been an hour earlier.

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

Wish we had music during take off and landing like the last flight

Crew is ok. They offered food n drinks. Had difficulty connecting to wifi on board.

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.

Flight was smooth and comfortable. The crew were exceptional. Amanda, Nichole and Hershel were attentive to our every need. So friendly. My daughter and I were surprised at quality of service. Loved the double row seating. Snacks were delicious. We would definitely fly with Porter again. Flight PD 670 SFO to YYZ Thank you so much for the best flight experience we have had

The E195-E2 is a great aircraft! Leather seats, lots of legroom and SO quiet! The flight crew is terrific!

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.

Flight delayed 6 hr. Looking for compensation and will claim for it.allow US people to fix to avoid huge delay having a canadian tech to fix it.

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.

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.
9/14Sat
1 stopDelta
5h 04mJFK-MDW
9/17Tue
1 stopDelta
4h 18mMDW-JFK
$524
9/7Sat
1 stopDelta
7h 58mJFK-MDW
9/14Sat
1 stopDelta
4h 41mMDW-JFK
$527
9/18Wed
1 stopDelta
4h 16mBOS-MDW
9/24Tue
1 stopDelta
4h 51mMDW-BOS
$546
6/12Wed
1 stopDelta
4h 28mBOS-MDW
6/17Mon
1 stopDelta
5h 11mMDW-BOS
$554
10/1Tue
1 stopDelta
4h 15mBOS-MDW
10/8Tue
1 stopDelta
4h 51mMDW-BOS
$556
7/23Tue
1 stopDelta
5h 11mJFK-MDW
7/27Sat
1 stopDelta
4h 47mMDW-JFK
$565
6/11Tue
1 stopDelta
6h 13mJFK-MDW
6/17Mon
1 stopDelta
4h 41mMDW-JFK
$570
8/20Tue
1 stopDelta
5h 29mIAD-MDW
8/21Wed
1 stopDelta
4h 29mMDW-IAD
$578
8/20Tue
1 stopDelta
3h 37mDCA-MDW
8/24Sat
1 stopDelta
4h 11mMDW-DCA
$578
9/7Sat
1 stopDelta
5h 02mJFK-MDW
9/9Mon
1 stopDelta
4h 18mMDW-JFK
$590
7/30Tue
1 stopDelta
4h 58mBOS-MDW
8/6Tue
1 stopDelta
5h 07mMDW-BOS
$590
8/28Wed
1 stopDelta
5h 32mJFK-MDW
9/2Mon
1 stopDelta
4h 47mMDW-JFK
$595
7/9Tue
1 stopDelta
4h 18mBOS-MDW
7/16Tue
1 stopDelta
5h 07mMDW-BOS
$600
7/2Tue
1 stopDelta
4h 29mBOS-MDW
7/6Sat
1 stopDelta
5h 14mMDW-BOS
$607
6/11Tue
1 stopDelta
6h 13mJFK-MDW
6/14Fri
1 stopDelta
4h 41mMDW-JFK
$611
7/10Wed
1 stopDelta
5h 11mJFK-MDW
7/13Sat
1 stopDelta
4h 47mMDW-JFK
$616
9/26Thu
1 stopDelta
6h 36mJFK-MDW
9/30Mon
1 stopDelta
4h 18mMDW-JFK
$620
7/1Mon
1 stopDelta
3h 39mIAD-MDW
7/10Wed
1 stopDelta
4h 31mMDW-IAD
$640
7/30Tue
1 stopDelta
4h 59mBOS-MDW
8/6Tue
1 stopDelta
5h 07mMDW-BOS
$644
11/14Thu
1 stopDelta
4h 15mBOS-MDW
11/19Tue
1 stopDelta
4h 51mMDW-BOS
$650

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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.
9/5Thu
1 stopDelta
4h 18mBOS-MDW
$273
10/16Wed
1 stopDelta
3h 26mIAD-MDW
$294
10/16Wed
1 stopDelta
3h 31mDCA-MDW
$294
6/15Sat
1 stopDelta
5h 05mJFK-MDW
$303
9/9Mon
1 stopDelta
6h 36mJFK-MDW
$308
7/24Wed
1 stopDelta
3h 28mIAD-MDW
$333
7/25Thu
1 stopDelta
3h 28mIAD-MDW
$351
7/24Wed
1 stopDelta
3h 37mDCA-MDW
$351
7/1Mon
1 stopDelta
3h 44mEWR-MDW
$353
6/15Sat
1 stopDelta
3h 43mEWR-MDW
$363
9/9Mon
1 stopDelta
3h 51mEWR-MDW
$368
9/5Thu
1 stopDelta
4h 18mBOS-MDW
$372
7/1Mon
1 stopDelta
5h 06mJFK-MDW
$408
6/21Fri
1 stopDelta
3h 38mIAD-MDW
$410
6/17Mon
1 stopDelta
3h 43mEWR-MDW
$458
6/21Fri
1 stopDelta
4h 39mIAD-MDW
$476
6/21Fri
1 stopDelta
5h 29mDCA-MDW
$476
6/6Thu
nonstopDelta
1h 50mATL-MDW
$486
6/6Thu
1 stopDelta
4h 06mATL-MDW
$495
7/25Thu
1 stopDelta
3h 33mDCA-MDW
$526

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Flights to Chicago Midway Airport

Destination:

Chicago Midway (MDW)United States

Return flight deals:

Chicago Midway - United States

Cabin classes:

$360
$433
$246
$43

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