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Find First Class Flights to Chicago

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Wed 7/3
Wed 7/10

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 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 5939 reviews
8.7Crew
7.3Food
8.3Boarding
8.1Comfort
7.8Entertainment
Airline reviews

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.

8.0 ExcellentMichelle, Jun 2024MDW - SEA
Read more about Southwest reviews

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

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 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.

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.

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.

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.

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

Overall fine but both ways for this trip was delayed.

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.

I had back trouble prior to my flight and everyone was great about helping me.

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.

My tv was broken on the flight which is disappointing when you pay for a seat and expect a service

Always delays from Boston to Salt lake but this time was very long. Don’t understand while they board the passengers and then make them sit in the plane

Service for food to our seat was a bit slow. Snack choices were just pretzels or baked chips. My seat cushion was not attached. Other than Barbie, video choice were not very good or current.

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

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

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.
8/20Tue
nonstopDelta
2h 59mBOS-ORD
8/21Wed
nonstopDelta
2h 26mORD-BOS
$379
8/26Mon
nonstopUnited Airlines
2h 28mDFW-ORD
9/10Tue
nonstopUnited Airlines
2h 37mORD-DFW
$389
8/20Tue
nonstopDelta
2h 59mBOS-ORD
8/22Thu
nonstopDelta
2h 26mORD-BOS
$393
8/21Wed
nonstopUnited Airlines
2h 49mBOS-ORD
8/21Wed
nonstopUnited Airlines
2h 29mORD-BOS
$402
8/21Wed
nonstopUnited Airlines
2h 47mBOS-ORD
8/27Tue
nonstopUnited Airlines
2h 29mORD-BOS
$407
8/20Tue
nonstopDelta
2h 59mBOS-ORD
8/23Fri
nonstopDelta
2h 29mORD-BOS
$414
7/24Wed
nonstopAmerican Airlines
2h 40mLGA-ORD
7/27Sat
nonstopAmerican Airlines
2h 04mORD-LGA
$417
6/18Tue
nonstopDelta
3h 01mJFK-ORD
7/26Fri
nonstopDelta
2h 41mORD-JFK
$418
11/22Fri
nonstopDelta
3h 05mJFK-ORD
12/4Wed
nonstopDelta
2h 20mORD-JFK
$422
8/21Wed
nonstopUnited Airlines
2h 47mBOS-ORD
8/25Sun
nonstopUnited Airlines
2h 26mORD-BOS
$427
8/22Thu
nonstopDelta
2h 59mBOS-ORD
8/23Fri
nonstopDelta
2h 29mORD-BOS
$428
7/2Tue
nonstopDelta
2h 45mJFK-ORD
7/9Tue
nonstopDelta
2h 20mORD-JFK
$437
8/22Thu
1 stopUnited Airlines
4h 46mBOS-ORD
8/24Sat
nonstopUnited Airlines
2h 29mORD-BOS
$437
7/20Sat
nonstopDelta
2h 46mJFK-ORD
7/30Tue
nonstopDelta
2h 41mORD-JFK
$438
7/3Wed
nonstopAmerican Airlines
2h 34mLGA-ORD
7/6Sat
nonstopAmerican Airlines
2h 04mORD-LGA
$440
7/2Tue
1 stopAmerican Airlines
4h 38mLGA-ORD
7/2Tue
nonstopAmerican Airlines
2h 06mORD-LGA
$444
7/2Tue
1 stopUnited Airlines
4h 37mEWR-ORD
7/2Tue
nonstopUnited Airlines
2h 32mORD-EWR
$446
7/23Tue
nonstopUnited Airlines
2h 36mDFW-ORD
7/27Sat
nonstopUnited Airlines
2h 33mORD-DFW
$447
8/18Sun
nonstopUnited Airlines
2h 46mBOS-ORD
8/26Mon
nonstopUnited Airlines
2h 26mORD-BOS
$447
7/20Sat
nonstopDelta
2h 46mJFK-ORD
8/2Fri
nonstopDelta
2h 41mORD-JFK
$448

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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
9/24Tue
nonstopUnited Airlines
2h 34mDFW-ORD
$195
7/2Tue
nonstopAmerican Airlines
2h 34mLGA-ORD
$209
6/12Wed
nonstopDelta
2h 44mJFK-ORD
$219
8/6Tue
nonstopAmerican Airlines
4h 09mSEA-ORD
$240
6/12Wed
nonstopDelta
2h 56mLGA-ORD
$240
9/11Wed
nonstopAmerican Airlines
4h 09mSEA-ORD
$241
7/2Tue
1 stopAmerican Airlines
6h 10mLGA-ORD
$241
6/9Sun
nonstopAmerican Airlines
2h 34mEWR-ORD
$259
6/16Sun
nonstopAmerican Airlines
2h 34mEWR-ORD
$261
6/10Mon
nonstopAmerican Airlines
2h 34mEWR-ORD
$269
6/19Wed
1 stopAmerican Airlines
5h 12mLGA-ORD
$272
9/24Tue
1 stopDelta
5h 26mDFW-ORD
$273
6/19Wed
1 stopAmerican Airlines
5h 30mJFK-ORD
$277
7/24Wed
nonstopUnited Airlines
2h 13mDCA-ORD
$280
8/12Mon
nonstopUnited Airlines
2h 10mDCA-ORD
$285
10/16Wed
nonstopUnited Airlines
2h 10mDCA-ORD
$286
8/13Tue
1 stopDelta
3h 36mDCA-ORD
$289
6/9Sun
nonstopUnited Airlines
2h 35mLGA-ORD
$289
8/12Mon
1 stopDelta
5h 34mDCA-ORD
$294

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Flights to Chicago

Return flight deals:

Chicago - United States

Cabin classes:

$360
$419
$234
$43

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