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Find First Class Flights to Chicago

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Fri 7/5
Fri 7/12

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 5922 reviews
8.1Comfort
7.3Food
8.7Crew
8.3Boarding
7.8Entertainment
Airline reviews

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

2.0 MediocreMatt, Jun 2024PHX - AUS
Read more about Southwest reviews

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

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

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.

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.

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.

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.

The walk from baggage claim to the taxi is very difficult for older people I will never fly into JFK again. It is physically challenging

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,

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

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.
7/3Wed
nonstopAmerican Airlines
2h 39mLGA-ORD
7/3Wed
1 stopAmerican Airlines
12h 16mORD-LGA
$359
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 34mORD-DFW
$389
8/24Sat
nonstopDelta
2h 56mJFK-ORD
8/27Tue
nonstopDelta
2h 41mORD-JFK
$408
7/2Tue
nonstopAmerican Airlines
2h 34mLGA-ORD
7/9Tue
nonstopAmerican Airlines
2h 21mORD-LGA
$417
8/7Wed
nonstopUnited Airlines
2h 50mBOS-ORD
8/10Sat
nonstopUnited Airlines
2h 22mORD-BOS
$417
8/26Mon
nonstopDelta
3h 02mJFK-ORD
8/27Tue
nonstopDelta
2h 41mORD-JFK
$418
9/25Wed
nonstopUnited Airlines
2h 28mDFW-ORD
9/29Sun
nonstopUnited Airlines
2h 37mORD-DFW
$418
7/6Sat
nonstopDelta
2h 45mJFK-ORD
7/16Tue
nonstopDelta
2h 41mORD-JFK
$437
8/24Sat
nonstopDelta
2h 56mJFK-ORD
8/26Mon
nonstopDelta
2h 16mORD-JFK
$438
7/8Mon
nonstopDelta
2h 46mJFK-ORD
7/13Sat
nonstopDelta
2h 41mORD-JFK
$440
6/15Sat
1 stopAmerican Airlines
18h 18mLGA-ORD
6/16Sun
nonstopAmerican Airlines
2h 12mORD-LGA
$440
8/24Sat
nonstopDelta
2h 56mJFK-ORD
8/29Thu
nonstopDelta
2h 41mORD-JFK
$442
9/29Sun
nonstopUnited Airlines
2h 21mDFW-ORD
10/4Fri
nonstopUnited Airlines
2h 37mORD-DFW
$447
11/25Mon
nonstopUnited Airlines
2h 56mBOS-ORD
12/3Tue
nonstopUnited Airlines
2h 23mORD-BOS
$447
6/15Sat
nonstopDelta
3h 01mJFK-ORD
7/23Tue
nonstopDelta
2h 41mORD-JFK
$448
7/9Tue
nonstopUnited Airlines
2h 30mDFW-ORD
7/12Fri
nonstopUnited Airlines
2h 33mORD-DFW
$449
8/22Thu
nonstopAmerican Airlines
2h 30mLGA-ORD
8/27Tue
1 stopAmerican Airlines
4h 18mORD-LGA
$450
8/26Mon
nonstopDelta
3h 02mJFK-ORD
8/29Thu
nonstopDelta
2h 16mORD-JFK
$452
6/15Sat
nonstopDelta
3h 01mJFK-ORD
7/26Fri
nonstopDelta
2h 41mORD-JFK
$458

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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
8/20Tue
nonstopUnited Airlines
2h 32mDFW-ORD
$195
9/26Thu
nonstopDelta
2h 45mBOS-ORD
$204
6/17Mon
nonstopDelta
3h 01mJFK-ORD
$219
6/18Tue
1 stopUnited Airlines
6h 55mBOS-ORD
$220
8/20Tue
1 stopUnited Airlines
4h 36mDFW-ORD
$223
6/16Sun
nonstopDelta
2h 57mBOS-ORD
$225
8/22Thu
nonstopAmerican Airlines
2h 38mEWR-ORD
$240
8/6Tue
nonstopAmerican Airlines
4h 09mSEA-ORD
$240
11/13Wed
nonstopDelta
2h 42mLGA-ORD
$240
6/19Wed
nonstopAmerican Airlines
4h 15mSEA-ORD
$249
6/16Sun
1 stopAmerican Airlines
5h 09mBOS-ORD
$250
6/13Thu
nonstopDelta
2h 45mJFK-ORD
$259
6/17Mon
nonstopAmerican Airlines
2h 37mEWR-ORD
$259
6/23Sun
nonstopAmerican Airlines
2h 37mEWR-ORD
$261
11/13Wed
1 stopDelta
4h 32mJFK-ORD
$262
8/9Fri
nonstopAmerican Airlines
2h 37mEWR-ORD
$262
11/13Wed
1 stopDelta
4h 31mEWR-ORD
$263
6/23Sun
nonstopAmerican Airlines
2h 34mLGA-ORD
$263
6/20Thu
nonstopDelta
2h 35mLGA-ORD
$268

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Flights to Chicago

Return flight deals:

Chicago - United States

Cabin classes:

$357
$312
$246
$44

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