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Find First Class Flights to Chicago

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Sat 7/6
Sat 7/13

Good to Know - First Class Flights to Chicago

Low season

January

High season

May

Average price round-trip

$1,193

Good deal round-trip

$493

Good deal one-way

$299
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 2% 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 5918 reviews
8.1Comfort
8.3Boarding
7.3Food
7.8Entertainment
8.7Crew
Airline reviews

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.

10.0 ExcellentMarybeth, May 2024LAS - ORD
Read more about Southwest reviews

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.

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.

The flight itself was good. We were delayed 1 1/2 hours which was not good.

Flight was fine but new boarding policy was a drag Xtra time passenger group And Waiting until entire bridge empties before calling a list preferred... Waste of time

Wish that they would space out the boarding a little. COVID is still around and is real. No entertainment. Miss the peanuts.

Excellent! There was a delay due to the weather and they did all they could do to keep us comfortable & updated. Thank you!

Cramped older 737. Noisy passengers nearby. Wish you would change and make KC a hub with a direct from OKC. Best new airport!

Planes never have enough leg room for someone my height so my knees were cramped and therefore started aching. Also, the Wi-Fi was down so I couldn't watch anything on my phone like I anticipated.

Flight was cancelled just before we boarded. I had to stayed an extra night in SF and arrived one day late. Also I had to flight back JFK and not Newark since they didn't have flight to Newark until very late the following day. A real bad experience on this flight. It took me 2 days to get back home.

Plane was very cold, but other than that, it was a perfect flight

I was sitting in row 31 and felt bad smell coming from the toilets especially when boarding and exiting not much during the flight.

The flight was delayed by more than two hours. A notification ahead of time would be most helpful.

Great. They got us on an earlier flight. Really appreciated that

I had very little legroom and the only food available was really salty

The airline itself was extremely comfortable and the staff were wonderful. The communication was excellent amongst the pilots and flight attendants and the passengers. I was throughly impressed by the cleaning crew that came on the plane immediately to ready it for the next flight. I have flown a bunch of times post Covid pandemic and have never seen this! I gave the “okay” rating for the food and entertainment because I didn’t order food and there wasn’t entertainment offered through the plane (only your personal devices).

Offer snacks/meals for people with food sensitivities. HAVE TV SCREENS!

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.

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!

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.

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.

Another horrible Jet Blue experience. This airline has suffered the biggest decline of all from best to worst. TVs didn’t work (again). internet was temperamental. Boarded late and couldn’t get organized to serve snacks.

I hate their constant delays! It’s as if I cannot confidently make plans for timing when I'm traveling with them. I slept through it, so all I can say is it was good.

From bag drop to boarding, it was great. In-flight is a little different. The seats were a little uncomfortable for that long of a flight. The rest of the cabin crew except for Eva was wonderful. Eva was not friendly at all. I've had to personally encounter her twice in-flight. First time was when I had to go to the lavatory in the back of the plane, and since it was the first for me to board such tiny plane, I didn't know we were using the crew toilet. She was giving me an attitude while telling me where and how to open it since it's not the regular push to open type of door. The second one was when I had to throw trash then use the lavatory again. I asked where to throw them, and unfortunately she was the only crew in the back doodling on her phone, she had to point it out to me with an attitude then told me to wait on the carpet, which I understand because I didn't realize that, but she could have been nicer. After all, I'm a paying customer, and assisting a passenger who isn't knowledgeable about the aircraft is one of the things she's there for. The rest of the experience and crew from bag drop to in-flight were excellent except for her.

It took an hour to get my bag after landing. Not exaggerating

We flew halfway to our destination (NYC to Burlington) and turned around due to a mechanical issue (landing gear wouldn’t retract automatically). We turned back to JFK for JetBlue’s benefit as we landed safely at JFK and could've just as easily landed safely in Burlington on our Christmas Day flight. Instead the company directed the crew to return the plane to more easily service the aircraft. The passengers landed 3 1/2 hours later and JetBlue gave each passenger $50 for the trouble. Hardly fair compensation to be separated from family on Christmas Day.

I had a horrible experience with TSA at the airport. I had to go through TSA several times as there was some issue each time with a piece if clothing I had on. It was so busy & chaotic that I ended up forgetting my Apple laptop at TSA. It’s been days & I can’t get through to anyone to get useful info on how to get it back. I’m very angry because contacting lost & found shouldn’t be this difficult. Employees should know what is going on at their place of work. It seems no one knows as everyone’s answers are contradictory, or you can’t speak directly to anyone as the calls are automated. Very upsetting.

No food/drink were offered. There was no Flyfi service. The screen size & quality were below JetBlue’s typical standards. The flight was delayed by an hour.

Everything was good instead change the gates! I missed my first flight because it was changed the gate and I didn’t know!

The new seats JetBlue uses angle downwards, so the entire flight you are sliding forward out of your own seat. These seats suck!

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.

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.
10/1Tue
nonstopUnited Airlines
2h 21mDFW-ORD
10/1Tue
nonstopUnited Airlines
2h 34mORD-DFW
$384
9/25Wed
nonstopUnited Airlines
2h 28mDFW-ORD
10/1Tue
nonstopUnited Airlines
2h 36mORD-DFW
$389
9/7Sat
nonstopUnited Airlines
2h 28mDFW-ORD
9/18Wed
nonstopUnited Airlines
2h 37mORD-DFW
$407
8/10Sat
nonstopUnited Airlines
2h 36mDFW-ORD
8/14Wed
nonstopUnited Airlines
2h 33mORD-DFW
$408
7/29Mon
nonstopAmerican Airlines
2h 40mLGA-ORD
7/30Tue
nonstopAmerican Airlines
2h 21mORD-LGA
$417
6/17Mon
nonstopDelta
3h 01mJFK-ORD
7/26Fri
nonstopDelta
2h 41mORD-JFK
$418
9/9Mon
nonstopUnited Airlines
2h 28mDFW-ORD
9/17Tue
nonstopUnited Airlines
2h 37mORD-DFW
$418
9/8Sun
nonstopUnited Airlines
2h 31mDFW-ORD
9/21Sat
nonstopUnited Airlines
2h 37mORD-DFW
$427
9/7Sat
1 stopUnited Airlines
6h 46mDFW-ORD
9/18Wed
nonstopUnited Airlines
2h 37mORD-DFW
$428
11/25Mon
nonstopDelta
2h 47mJFK-ORD
12/6Fri
nonstopDelta
2h 47mORD-JFK
$433
6/17Mon
nonstopDelta
3h 01mJFK-ORD
6/18Tue
nonstopDelta
2h 21mORD-JFK
$437
9/9Mon
nonstopUnited Airlines
2h 29mDFW-ORD
9/22Sun
nonstopUnited Airlines
2h 37mORD-DFW
$438
7/8Mon
nonstopDelta
2h 46mJFK-ORD
7/13Sat
nonstopDelta
2h 41mORD-JFK
$440
7/29Mon
nonstopAmerican Airlines
2h 40mLGA-ORD
8/3Sat
nonstopAmerican Airlines
2h 21mORD-LGA
$440
7/6Sat
nonstopDelta
2h 45mJFK-ORD
7/9Tue
nonstopDelta
2h 20mORD-JFK
$447
9/8Sun
nonstopUnited Airlines
2h 31mDFW-ORD
9/22Sun
nonstopUnited Airlines
2h 37mORD-DFW
$447
9/7Sat
1 stopUnited Airlines
6h 46mDFW-ORD
9/22Sun
nonstopUnited Airlines
2h 37mORD-DFW
$448
6/18Tue
nonstopDelta
3h 01mJFK-ORD
7/22Mon
nonstopDelta
2h 16mORD-JFK
$452
6/21Fri
nonstopDelta
2h 58mJFK-ORD
7/24Wed
nonstopDelta
2h 41mORD-JFK
$453
7/5Fri
nonstopUnited Airlines
2h 30mDFW-ORD
7/12Fri
nonstopUnited Airlines
2h 33mORD-DFW
$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.
11/13Wed
nonstopDelta
3h 05mJFK-ORD
$190
6/17Mon
nonstopDelta
3h 01mJFK-ORD
$219
7/3Wed
nonstopAmerican Airlines
2h 34mLGA-ORD
$232
7/13Sat
nonstopDelta
2h 59mLGA-ORD
$240
6/20Thu
1 stopAmerican Airlines
4h 54mLGA-ORD
$241
7/13Sat
nonstopAmerican Airlines
2h 37mEWR-ORD
$246
6/19Wed
nonstopAmerican Airlines
4h 15mSEA-ORD
$249
7/8Mon
nonstopAmerican Airlines
2h 35mEWR-ORD
$261
6/20Thu
nonstopAmerican Airlines
2h 34mLGA-ORD
$263
7/13Sat
nonstopDelta
2h 46mJFK-ORD
$264
7/8Mon
nonstopDelta
2h 47mLGA-ORD
$264
7/3Wed
nonstopDelta
2h 58mJFK-ORD
$269
7/13Sat
1 stopAmerican Airlines
5h 46mEWR-ORD
$270
8/4Sun
nonstopUnited Airlines
2h 37mLGA-ORD
$270
7/13Sat
1 stopAmerican Airlines
7h 41mLGA-ORD
$272
11/13Wed
1 stopDelta
6h 40mEWR-ORD
$274
11/13Wed
1 stopDelta
4h 32mJFK-ORD
$278
7/13Sat
1 stopDelta
5h 10mJFK-MDW
$278
7/3Wed
nonstopAmerican Airlines
2h 37mEWR-ORD
$294
7/3Wed
1 stopAmerican Airlines
5h 12mLGA-ORD
$302

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Flights to Chicago

Return flight deals:

Chicago - United States

Cabin classes:

$357
$312
$246
$44

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