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Find First Class Flights to Chicago

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Sat 6/29
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Good to Know - First Class Flights to Chicago

Low season

January

High season

May

Average price round-trip

$3,648

Good deal round-trip

$702

Good deal one-way

$303
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 5956 reviews
8.3Boarding
7.3Food
8.1Comfort
8.7Crew
7.8Entertainment
Airline reviews

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.

2.0 MediocrePeter, May 2024OMA - DEN
Read more about Southwest reviews

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.

Because of storms in St Louis, plane was diverted to Kansas City. After about 1 hour stay went back to st Louis to finally reach distanation. Made for long day. But southwest took care of us. Can't fight mother nature

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

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

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.
9/3Tue
nonstopDelta
2h 56mJFK-ORD
9/9Mon
nonstopDelta
2h 20mORD-JFK
$399
9/1Sun
nonstopDelta
2h 46mJFK-ORD
9/4Wed
nonstopDelta
2h 41mORD-JFK
$422
7/1Mon
nonstopUnited Airlines
2h 50mBOS-ORD
7/4Thu
nonstopUnited Airlines
2h 30mORD-BOS
$429
7/24Wed
nonstopDelta
3h 01mJFK-ORD
7/29Mon
nonstopDelta
2h 16mORD-JFK
$438
9/5Thu
nonstopDelta
2h 56mJFK-ORD
9/6Fri
nonstopDelta
2h 41mORD-JFK
$445
10/15Tue
nonstopUnited Airlines
2h 47mBOS-ORD
10/21Mon
nonstopUnited Airlines
2h 26mORD-BOS
$447
9/6Fri
nonstopDelta
2h 56mJFK-ORD
9/11Wed
nonstopDelta
2h 20mORD-JFK
$448
9/3Tue
nonstopAmerican Airlines
2h 30mLGA-ORD
9/11Wed
1 stopAmerican Airlines
4h 09mORD-LGA
$449
7/29Mon
1 stopAmerican Airlines
5h 01mLGA-ORD
7/31Wed
nonstopAmerican Airlines
2h 21mORD-LGA
$450
10/15Tue
1 stopUnited Airlines
6h 55mBOS-ORD
10/21Mon
nonstopUnited Airlines
2h 26mORD-BOS
$457
9/4Wed
nonstopDelta
3h 02mJFK-ORD
9/7Sat
1 stopDelta
5h 02mORD-JFK
$461
7/17Wed
nonstopUnited Airlines
2h 50mBOS-ORD
7/21Sun
nonstopUnited Airlines
2h 22mORD-BOS
$462
9/1Sun
nonstopDelta
2h 47mLGA-ORD
9/4Wed
nonstopDelta
2h 16mORD-LGA
$479
6/15Sat
1 stopAmerican Airlines
7h 40mLGA-ORD
6/16Sun
1 stopAmerican Airlines
3h 52mORD-LGA
$481
6/13Thu
1 stopAmerican Airlines
4h 54mLGA-ORD
6/20Thu
1 stopAmerican Airlines
5h 28mORD-LGA
$482
6/15Sat
nonstopDelta
3h 01mJFK-ORD
7/23Tue
nonstopDelta
2h 41mORD-JFK
$483
9/1Sun
1 stopDelta
6h 11mJFK-ORD
9/4Wed
nonstopDelta
2h 16mORD-JFK
$485
7/23Tue
nonstopAmerican Airlines
2h 49mEWR-ORD
7/27Sat
nonstopAmerican Airlines
2h 10mORD-EWR
$485
7/30Tue
nonstopDelta
3h 01mJFK-ORD
8/2Fri
nonstopDelta
2h 41mORD-JFK
$487
8/12Mon
1 stopAmerican Airlines
7h 14mSEA-ORD
8/16Fri
nonstopAmerican Airlines
4h 46mORD-SEA
$489

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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.
6/5Wed
nonstopDelta
2h 42mJFK-ORD
$206
6/6Thu
nonstopUnited Airlines
2h 50mBOS-ORD
$217
6/13Thu
nonstopAmerican Airlines
2h 56mBOS-ORD
$226
6/26Wed
nonstopAmerican Airlines
2h 34mLGA-ORD
$232
7/8Mon
nonstopAmerican Airlines
2h 35mEWR-ORD
$239
6/20Thu
nonstopAmerican Airlines
4h 15mSEA-ORD
$240
7/29Mon
nonstopDelta
2h 47mLGA-ORD
$240
7/9Tue
nonstopAmerican Airlines
2h 49mEWR-ORD
$241
6/26Wed
1 stopAmerican Airlines
6h 04mLGA-ORD
$241
6/29Sat
nonstopAmerican Airlines
2h 37mEWR-ORD
$246
7/20Sat
nonstopDelta
2h 46mJFK-ORD
$249
6/12Wed
nonstopAmerican Airlines
4h 15mSEA-ORD
$249
8/25Sun
nonstopDelta
2h 56mJFK-ORD
$253
6/5Wed
nonstopAmerican Airlines
2h 40mEWR-ORD
$259
6/13Thu
1 stopAmerican Airlines
4h 42mBOS-ORD
$260
7/8Mon
nonstopAmerican Airlines
2h 35mEWR-ORD
$261
6/5Wed
1 stopDelta
6h 22mJFK-ORD
$263
7/8Mon
nonstopDelta
2h 47mLGA-ORD
$263
6/5Wed
nonstopAmerican Airlines
2h 34mLGA-ORD
$266
6/16Sun
1 stopAmerican Airlines
4h 55mEWR-ORD
$269

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Flights to Chicago

Return flight deals:

Chicago - United States

Cabin classes:

$360
$419
$234
$43

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