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Find Business Class Flights to Chicago Midway Airport

1 adult
0 bags
mar 7/9
mar 7/16

When to book business class flights to Chicago Midway Airport

Are your dates flexible? We break down the daily and monthly prices for business 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 business 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 business 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 business class flights

  • How long is a flight to Chicago Midway Airport?

    Flights from Phoenix3h 35m
    Flights from Baltimore1h 54m
    Flights from Tampa2h 41m
    Flights from Orlando2h 44m
    Flights from Miami3h 06m
  • How does KAYAK find such good deals on Business 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 Business Class travelers.

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

    The highest-rated airline by KAYAK users offering business class flights to Chicago Midway Airport is Delta, with an overall rating of 8.0.

Top tips for finding business class flights to Chicago Midway Airport

  • The most expensive day to fly Business Class to Chicago Midway Airport is Thursday, while the cheapest is Wednesday.

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 business 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 5905 reviews
8.1Comfort
7.3Food
8.7Crew
8.3Boarding
7.8Entertainment
Airline reviews

Flights were full but SWA still managed to get everyone loaded and depart on time. No snack or beverage service on the first leg due to turbulance. Seats were clean but very little cushioning. Reasonable amount of leg room.

10.0 ExcellentJames, Jun 2024OAK - DEN
Read more about Southwest reviews

Flights were full but SWA still managed to get everyone loaded and depart on time. No snack or beverage service on the first leg due to turbulance. Seats were clean but very little cushioning. Reasonable amount of leg room.

AC wasn't working then we sat on the tarmac in Austin for 40 minutes waiting for a gate.

Had a long layover in rainy Chicago. The staff were attentive - my husband needed a wheelchair due to a recent fall and unsteady on his feet. They are wonderful for those of us who need a bit of extra care. My only complaint was discovered upon unpacking our suitcases at home. One (we had 3 carry on size and one just a bit larger) had water damage to everything inside. All the clothing (just happened to be the case with the clean clothes) were wet. I know it was raining, but why would items inside be wet? The paperwork packed in this case was damp with ink running. There were momentos from our 10-day European vacation that I was hoping to scrapbook - but alas, they will be scrapped - too damaged to keep. The boxes of French chocolate were damp on the outside. My expensive camera now has a cracked screen and a Gaudi tea-for-one was cracked - even though it was packed in clothing. I know it happened on this flight as I repacked all four suitcases before leaving New York in the morning. My first unhappy experience with luggage at Southwest.

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

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

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.

Our first flight was so delayed that we had 10 mins to board the next one. We requested if the flight attendant could allow us off there plane first and they denied our request even though I have seen this done before. Luck was on our side that we didn’t miss our next flight.

Delay after delay after delay. Very disappointing I am about ready to give up on Southwest. One of the crewmembers sat and played games on her phone for the entire trip from Chicago to Baltimore. Unbelievable, very unprofessional, and very disappointing.

Not good.,At first delayed due to weather, then still had to load all the luggage, then a mechanical issue. Upon finally arriving, clothes wet as suitcases sat out in the rain. In a hard side suitcase! Ruined some paper items inside. Not happy!

As always it was a pleasure to fly on southwest.

3 hours late and all they have is was a $12 meal voucher. That’s not even enough to cover fast food.

Among the poorest flights I’ve had with Delta in a while. Entertainment system failed completely on a 7.5 hr flight. Crew seemed distracted and not the normal friendly crew. Flight overbooked it seemed… very crowded.

If I can, I always fly Delta. I’ve found their service to always be reliable and pleasant.

You could have not cancelled the flight (AA, which I will be flying from now on) left for BOS despite the fictitious weather issues (that no one in my Boston family could see). You could have rebooked my direct flight to another direct flight instead of sending me though JFK, the worst US airport after O’Hara You could have rebooked me on a Main Cabin seat (like the one I paid for in my original ticket instead of putting me a the last row on JFK->BOS leg, pocketing the difference in ticket price But I do not really care whether you will ever do that in a future because in a future neither I nor anyone from my company (unless they pay out of pocket) nor an of my clients and partners (if they heed my advice) will ever be caught dead on any of Delta flights

Really bad baggage handling. Had my Rimowa bag badly damaged at the latches.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

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!

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.

They lost our luggage and didn’t return it until 15 days AFTER we got back.

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.

If they have a tv for movie or map during 5h flight could be better and the food can purchase on flight are ok with that.

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.

Flight was good, boarding was a breeze, flight attendants were friendly and professional. There was a medical issue with another passenger and the crew handled it in a calm and professional way.

The net issue I had was with the gate agent. We had added a carryon to our boarding pass when we checked bags. When I got to the boarding gate the agent was rude asking why I had a backpack - I said I added it - even had an orange tag on it. She ripped my tag off and swung her monitor around to show me how she was right- saying it isn’t wasn’t listed - only a checked bag. I explained again that I wasn’t sure what the issue was but I wouldn’t have an orange tag if I hadn’t added it. Then she finally checked my husband’s boarding pass and found that the agent at checkin had added my carryon to his boarding pass instead of mine. She sent me on my way without my orange tag. Was a bit embarrassing for me the tone she used with me assuming I was trying to get away with something.

Gate agent asked if I could switch seats so a family could sit together. Agent moved me to a seat in the front of the plane, no charge. It was easy. The agent did a great job.

Great seat space. However food and drink prices outrageous. Jabbing to pay for a carry on bag or stuck paying at the gate too much.

Every Allegiant Air flight I've ever taken has been delayed. This flight was delayed a full 2 hours. It was excuse after excuse after excuse. It was a flight from southern Florida. They made us board the plane on time, but made us wait for 2 hours on the tarmac. Because the engines were kept shut off, so was the air conditioning. One can only imagine how hot the air was in the cabin over those 2 hours on the tarmac, while in the hot Florida sun. Just terrible.

Actually, for the price, I'm willing to put up with a little discomfort (upright chairs) and at times inconveniences (like any airline), lack of entertainment (I can bring my own). My flight was non stop and smooth. I would fly this route again.

The flight was delayed 6 hours and we were only offered an $8 food credit. My husband stood in line to get the credit for 45 minutes and when he got close to the end of the line the computers went down.

Worst ever! Flight cancelled supposedly for weather even though we k ow of many others who flew into Bangor same time no problem. At the airport there was no customer service at all just refund and no possibility of rebook for 3-4 days. Aweful won’t fly with them again!!

It’s a budget airline so adjust expectations accordingly. Nothing is without a fee but such is necessary for tickets to remain so affordable.

No complaints. It’s a budget airline so can’t expect any frills.

Due to mechanical problems it was delayed causing problems the actual flight. Was fune

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.

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Flights to Chicago Midway Airport

Destination:

Midway (MDW)United States

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Midway - United States

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$433
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