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Find First Class Flights to Chicago

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Sun 7/7

Good to Know - First Class Flights to Chicago

Low season

January

High season

May

Average price round-trip

$2,726

Good deal round-trip

$685

Good deal one-way

$287
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 1% lower on average.
(avg. price over the last 2 weeks)
or less
or less

When to book first class flights to Chicago

Are your dates flexible? We break down the daily and monthly prices for first class flights to Chicago, 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 first class flights

  • Which airline has the best first class amenities for flights to Chicago?

    If you reserve a first class flight to Chicago using American Airlines, you will have access to some of the world's best amenities. These range from their cozy, spacious, and luxurious seats to delicious meals and unlimited entertainment. First class passengers use seats with more legroom, ensuring their comfort the entire journey. Passengers are also served a variety of freshly prepared meals accompanied by drinks.

  • Which airline has the best flatbeds for first class flights to Chicago?

    American Airlines has the best flatbeds for first class flights to Chicago. The passengers are able to conveniently adjust their seats to a fully horizontal position. Their property of being spacious makes it possible for them to take any shape. Additionally, the process of adjusting the position of the seat is quite easy; the passenger is only required to press the adjust button, and everything is done.

  • Which airline has the best first class lounge amenities for flights to Chicago?

    The American Airlines' first class lounge has the best amenities. These include the spacious dining where passengers enjoy a variety of freshly prepared meals served with a rich selection of drinks. The lounge also has large flat-screen televisions that offer them unlimited entertainment as they wait for the plane.

  • What is the most popular airline offering First Class flights to Chicago?

    Among KAYAK users, American Airlines is the most popular airline offering First Class seats on flights to Chicago.

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

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

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

    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 for economy class as well as First Class travelers.

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

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

See more FAQs

Top tips for finding first class flights to Chicago

  • Booking first class flights to Chicago through the Chicago O' Hare International Airport and Chicago Midway International Airport will give you the advantage of a shorter security line. This will ensure that you do not waste time before getting to your luxurious seat.
  • Travelers at the Chicago O' Hare International Airport will be able to access the first class lounge at Terminal 3. Those at the Chicago Midway International Airport will be able to access the first-class lounge at Terminal 1.
  • Passengers using first class flights to Chicago will be the first to alight when their plane lands at Chicago O' Hare International Airport or Chicago Midway International Airport. Their luggage will also undergo security checks before that of the other passengers. This increases their level of convenience.
  • The most expensive day to fly First Class to Chicago is Sunday, while the cheapest is Friday.
See more tips

Top 5 airlines flying to Chicago

 
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? 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
8.7Crew
8.1Comfort
7.8Entertainment
8.3Boarding
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 liked that I got home safe. The flight was 3 hours late because of a broken aircraft

4 hour delay and STILL sitting ON PLANE AT GATE. We were told 25 minutes ago it without be 2 minutes. Let me say that again.. 25 minutes AFTER they said 2 minutes. Well, at least we get free WiFi. Oh, wait.

Plane hit turbulence diverted to Houston. We'll probably get in after 3am

Cabin crew very friendly and pleasant. Flight left late but we didn't know why. Alaska Airlines app was not user friendly -- app wouldn't let us upgrade our seats, but no indication if flight was full. We wound up having to call the airline to request an upgrade and we were told none was available. Waste of time. Baggage retrieval was easy.

Given incorrect gate upon check-in, corrected by the gate attendant, D6 rather than D5, minor inconvenience. As with the previous flight, passengers were admonished to voluntarily gate-check carry-on luggage with the statement that those in the last boarding group would have no choice but to do so. If the Boeing 737 MAX8/MAX9 doesn't have room for carry-ons it's an interior design flaw on the part of Boeing. Posting an advance warning would be helpful, such as "Boeing 737 MAX planes feature limited carry-on space. Please be aware." SFO's amenities and TSA much better than MCO's. Crew was amazing! Brought my own food because Alaska's onboard selection has soy in everything. Beverage service was excellent. This was the first and last trip with Alaska after the previous flight's issues. It's no reflection on the crew of this flight. They were great.

The boarding gate is literally just an aisle to the concourse. There is no seating and it's shared with several other airlines. It's crowded, hot, and standing-room only. It's difficult to hear gate announcements over the PA system with too many other carriers crammed into a small space. I've enjoyed flying AA in the past on the west coast, but the BNA single gate experience is horrendous! Never again from BNA to SEA with AA.

It was a partial full flight. But even with a spare seat it was hard to get comfortable More on me being a wide body probably

Our flights using Alaska Airlines went great! All of the flight attendants were very friendly. Big shout out to the pilots for getting us to and from our destinations safely!

I can’t complain. Perhaps passing out headphones, but it was on me to bring my own since I could have used some for my personal device.

1309 on May had some very bumpy segments that seem to take too long to get to smoother air. My initial flight out of GRR was delayed and missed connections. Sure glad I made a different one in ORD so I could be in Anchorage.

I liked only the crew. The flyght was too much fast, faster than it should be, on 20 min faster, but not safer, I experienced on myself astranautic overload from suddenly appearing in the sky and all the vibrations of the turbines, because I had my place at the level of the wings. Pregnant woman should not be seated on the level of the wings with all turbines, pregnant woman should be offered to charge place to seat closer to front or in the back, but not at the level of all the turbines. Vibrations of turbines are not healthy for pregnancy. I hold all the flight my belly in my hands to avoid miscarriage. If it would be longer flying distances, I could have miscarriage with Alaskan airlines.

I didn't have food or use entertainment, so those evaluations are invalid.

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

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

Overall fine but both ways for this trip was delayed.

Flight was delayed by almost 5 hours. Suitcase was not loaded despite the flight being near empty (my colleagues’ suitcases did reach JFK, unlike mine). Had to argue on phone to get JetBlue to deliver the case to my hotel. Never again

The flight was excellent. The crew was welcoming and attentive.

Great! I love Jet Blue. My favorite airline! Very efficient, clean and timely.

Run out of snack choices. Why are the seats not padded for your butt? Are we sitting on blocks of wood or metal for $250-300 a pop? This ain’t spirit. Let’s get it together people

We were told that our flight would be delayed for 90+ minutes because of weather, so we went to get something to eat only to have them randomly start boarding 15 minutes after the announcement, with no warning.

Entertainment... No earphones passed out. Many including me couldn't use the TV. Legroom was good. Crew was indifferent and a bit surly. Free wifi was a nice convenience. Check in desk location was unknown. Gate number on the boarding passes was wrong.

Going through JFK’s security is a mess. The TSA security said no shoes on the bins. So, we place our shoes in the belt and they came out all over the belt. Boarding was delayed and Flight as well.

Safe and on time were the positives. The plane wasn't cleaned before boarding, there was garbage and food on the floor and in the seat pocket. The TV screen was small and the picture fuzzy, audio quality was poor. Seatbelt was fraying and seat did not recline properly. No charging ports near the seats,

Confusing. Delay updates were out of whack At one point it said my flight was 25 hours. Three gate changes and two delays only to change back to original departure time. Gate announcer and on board flight attendant (Alejandro) making the announcements was impossible to understand due to accent and speed of speech. After beverage service the rear flight attendants sat back there on their phones. No refills no checking in, one sweep through for trash collection. Very impersonal. Bring back Coke products

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.

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.

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

Book first class plane tickets to Chicago

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.
8/26Mon
nonstopUnited Airlines
2h 29mDFW-ORD
9/10Tue
nonstopUnited Airlines
2h 37mORD-DFW
$389
9/18Wed
nonstopDelta
2h 47mJFK-ORD
9/24Tue
nonstopDelta
2h 47mORD-JFK
$398
7/9Tue
nonstopUnited Airlines
2h 50mBOS-ORD
7/10Wed
nonstopUnited Airlines
2h 22mORD-BOS
$416
6/15Sat
nonstopDelta
3h 01mJFK-ORD
7/26Fri
nonstopDelta
2h 41mORD-JFK
$418
9/3Tue
nonstopDelta
2h 56mJFK-ORD
9/9Mon
nonstopDelta
2h 20mORD-JFK
$419
9/18Wed
nonstopDelta
2h 47mJFK-ORD
9/26Thu
nonstopDelta
2h 20mORD-JFK
$421
6/13Thu
nonstopUnited Airlines
2h 50mBOS-ORD
6/17Mon
nonstopUnited Airlines
2h 31mORD-BOS
$427
6/15Sat
nonstopDelta
3h 01mJFK-ORD
7/25Thu
nonstopDelta
2h 41mORD-JFK
$437
7/9Tue
nonstopUnited Airlines
2h 50mBOS-ORD
7/10Wed
1 stopUnited Airlines
6h 58mORD-BOS
$437
7/20Sat
nonstopDelta
2h 46mJFK-ORD
7/23Tue
nonstopDelta
2h 41mORD-JFK
$438
9/5Thu
nonstopUnited Airlines
2h 49mBOS-ORD
9/9Mon
nonstopUnited Airlines
2h 29mORD-BOS
$438
7/21Sun
nonstopAmerican Airlines
2h 38mLGA-ORD
7/26Fri
nonstopAmerican Airlines
2h 21mORD-LGA
$440
6/14Fri
nonstopDelta
2h 58mJFK-ORD
6/25Tue
nonstopDelta
2h 14mORD-JFK
$442
9/19Thu
nonstopDelta
2h 47mJFK-ORD
9/24Tue
nonstopDelta
2h 47mORD-JFK
$446
6/18Tue
1 stopUnited Airlines
5h 10mBOS-ORD
8/27Tue
1 stopUnited Airlines
6h 58mORD-BOS
$446
8/16Fri
nonstopUnited Airlines
2h 50mBOS-ORD
8/18Sun
nonstopUnited Airlines
2h 22mORD-BOS
$447
7/17Wed
nonstopDelta
3h 01mJFK-ORD
7/26Fri
nonstopDelta
2h 41mORD-JFK
$448
9/18Wed
nonstopAmerican Airlines
2h 35mLGA-ORD
9/25Wed
1 stopAmerican Airlines
5h 18mORD-LGA
$448
7/15Mon
1 stopAmerican Airlines
5h 01mLGA-ORD
7/20Sat
nonstopAmerican Airlines
2h 21mORD-LGA
$450
6/15Sat
nonstopDelta
3h 01mJFK-ORD
7/16Tue
nonstopDelta
2h 41mORD-JFK
$457

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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.
9/24Tue
nonstopUnited Airlines
2h 31mDFW-ORD
$195
9/5Thu
nonstopDelta
3h 00mBOS-ORD
$195
9/5Thu
nonstopDelta
3h 00mBOS-ORD
$200
8/26Mon
nonstopDelta
2h 58mBOS-ORD
$209
11/13Wed
nonstopDelta
3h 05mJFK-ORD
$210
6/26Wed
nonstopUnited Airlines
2h 50mBOS-ORD
$214
8/30Fri
nonstopUnited Airlines
2h 29mDFW-ORD
$215
9/24Tue
1 stopUnited Airlines
4h 36mDFW-ORD
$224
9/5Thu
1 stopUnited Airlines
4h 46mBOS-ORD
$224
6/24Mon
nonstopAmerican Airlines
2h 55mBOS-ORD
$226
8/26Mon
1 stopUnited Airlines
5h 23mBOS-ORD
$233
7/9Tue
nonstopAmerican Airlines
2h 49mEWR-ORD
$239
7/5Fri
nonstopAmerican Airlines
2h 49mEWR-ORD
$240
8/6Tue
nonstopAmerican Airlines
4h 09mSEA-ORD
$240
8/14Wed
nonstopDelta
2h 58mLGA-ORD
$240
6/17Mon
1 stopAmerican Airlines
4h 54mLGA-ORD
$241
6/10Mon
nonstopAmerican Airlines
2h 56mBOS-ORD
$241
6/27Thu
nonstopUnited Airlines
2h 50mBOS-ORD
$244
8/14Wed
nonstopDelta
3h 02mJFK-ORD
$249
6/14Fri
nonstopAmerican Airlines
4h 15mSEA-ORD
$249

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Flights to Chicago

Return flight deals:

Chicago - United States

Cabin classes:

$360
$419
$234
$43

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