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Find First Class Flights to Chicago

1 adult
0 bags
Mon 5/27
Mon 6/3

Good to Know - First Class Flights to Chicago

Low season

March

High season

June

Average price round-trip

$1,222

Good deal round-trip

$436

Good deal one-way

$236
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 28% increase in price.
(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 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 Monday, while the cheapest is Friday.
  • To get a below average price, try to book at least 1 week in advance of your departure date.
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 6165 reviews
8.3boarding
8.7crew
7.8entertainment
8.1comfort
7.4food
Airline reviews

Best domestic airline in the USA. Excellent fares and two bags included with every fare (only carrier to do so).

10.0 ExcellentAndrew, Apr 2024LAX - LAS
Read more about Southwest reviews

Best domestic airline in the USA. Excellent fares and two bags included with every fare (only carrier to do so).

The crew was fabulous, outstanding, friendly, attentive and just great, really made my flight one of the best I've ever had, thank you southwest crew flight #474, from Los Angeles to San Francisco on April 2,2024

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.

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.

Two hour delay including one of them on the tarmac second year in a row we’ve had a bad experience. Sad that Southwest is no longer a bargain and has failed to keep up the customer service they were once so famous for.

Wifi wasn't working well on the flight. Couldn't access entertainment options

I usually choose Alaska Airlines over any other airline. They try the hardest to make flying a great experience.

Staff being friendly would have help since the flight was delayed, again. Folks answered questions but no one seemed happy to be working today and if showed.

Quick easy boarding. Airport was unprepared for early landing and we were waiting in the plane for 20 minutes before getting a gate.

It was a full flight without any issues or stress. Really surprised with how so many flights seem to have issues nowadays.

Flight was good. Glad it was delayed or I may have missed the connection since I got to Seattle at about the same time my connection was to leave. The snack was a small bag of pretzels and a small soda. Can’t really call that food. There was no entertainment available on the flight.

Same as the earlier flight. Bad boarding practices, uncomfortable seats, and no Wi-Fi service.

Everything was good. One of the flight attendants was not very friendly

Text and wifi were paywalled. I'm not looking for something fast, but not getting a text for ride coordination until back at the gate was a pain.

I like that we took off on time and arrived a bit early. I like that I could gate check my bag and board early. I don't like how crowded the flight was. I had ok leg room, but could feel every move of the person next to me. And the aisles are very narrow. The gate and flight crews were terrific.

It was not a great flight. There was a software update delay which had us on the ground for almost 2 hours. I was unable to make my shuttle to my final destination.

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

They did a fine job. Can't wait to use Delta in the future.

Had a broken tray in business class. Crew just shrugged it off.

Seat back monitors and outlets were dead and not working.

Everything was great except for the seat. The backrest would not stay in the upright position.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

Service was good for such a short flight. Small plane but smooth flight.

The flight was delayed but we got to our final destination.

Seats in first class on the E175 recline too far back. I was in 2A, and the man in 1A fully reclined almost the entire flight. It took 6-7 inches of space away from me and made it very difficult to work on my laptop.

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

After we landed, we were held on the plane for 30 minutes. There was no one at the gate once we landed and we forced to sit on a plan that had already over an hour delayed.

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 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.

I had planned to watch the Westjet entertainment for the entire flight however, because the seat mounted outlets in our row did not work.

Over all good. I had some issues with trying to buy my seat. The Westjet system kept trying to charge my credit card, without getting the seat. In the end after 5 times being charged, I got my seat.

I did not have a meal or entertainment, but flight was comfortable, beverage service was quick, crew was very helpful and pleasant. And a very smooth flight overall.

Not a bad flight but our priority tagged luggage was the very last to come down the carousel.

Plane had a flat tire, delayed boarding and takeoff but one in the air, smooth. Make sure you have downloaded the WJ app before you leave. When on board, you can watch movies or TV shows offered on the app, it passed the time very quickly.

A good set of flights but my suitcase was irreparably damaged. (Hard shell suitcase with multiple full layer cracks from one corner all the way to the zipper) I needed to rush to catch a ferry so I didn’t notice it until it was loaded into a taxi. It cost over $100 USD to replace the suitcase to travel home.

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.
5/25Sat
nonstopDelta
2h 51mJFK-ORD
5/30Thu
nonstopDelta
2h 33mORD-JFK
$423
5/28Tue
nonstopUnited Airlines
2h 50mBOS-ORD
5/30Thu
nonstopUnited Airlines
2h 20mORD-BOS
$423
5/27Mon
nonstopDelta
2h 42mJFK-ORD
5/30Thu
nonstopDelta
2h 26mORD-JFK
$433
5/25Sat
nonstopDelta
2h 51mJFK-ORD
5/29Wed
nonstopDelta
2h 18mORD-JFK
$453
6/11Tue
nonstopUnited Airlines
2h 50mBOS-ORD
6/15Sat
nonstopUnited Airlines
2h 20mORD-BOS
$453
7/24Wed
nonstopUnited Airlines
2h 50mBOS-ORD
7/29Mon
nonstopUnited Airlines
2h 22mORD-BOS
$454
6/13Thu
nonstopDelta
2h 45mJFK-ORD
6/18Tue
nonstopDelta
2h 14mORD-JFK
$457
5/3Fri
nonstopDelta
2h 59mJFK-ORD
5/7Tue
nonstopDelta
2h 26mORD-JFK
$458
5/27Mon
nonstopDelta
2h 42mJFK-ORD
5/28Tue
nonstopDelta
2h 18mORD-JFK
$463
5/10Fri
nonstopDelta
2h 51mJFK-ORD
5/16Thu
nonstopDelta
2h 18mORD-JFK
$476
5/4Sat
1 stopDelta
5h 12mJFK-ORD
5/7Tue
nonstopDelta
2h 26mORD-JFK
$481
5/6Mon
nonstopDelta
2h 59mJFK-ORD
5/11Sat
1 stopDelta
4h 45mORD-JFK
$482
6/11Tue
1 stopUnited Airlines
4h 50mBOS-ORD
6/15Sat
nonstopUnited Airlines
2h 20mORD-BOS
$482
6/18Tue
nonstopDelta
2h 44mJFK-ORD
7/22Mon
nonstopDelta
2h 14mORD-JFK
$483
5/8Wed
1 stopDelta
6h 22mJFK-ORD
5/14Tue
nonstopDelta
2h 26mORD-JFK
$485
5/8Wed
nonstopDelta
2h 42mJFK-ORD
5/14Tue
nonstopDelta
2h 26mORD-JFK
$486
6/4Tue
nonstopUnited Airlines
2h 50mBOS-ORD
6/6Thu
nonstopUnited Airlines
2h 20mORD-BOS
$486
5/25Sat
1 stopUnited Airlines
5h 10mBOS-ORD
5/26Sun
nonstopUnited Airlines
2h 20mORD-BOS
$488
5/8Wed
1 stopAmerican Airlines
4h 53mEWR-ORD
5/14Tue
1 stopAmerican Airlines
5h 32mORD-EWR
$489
5/11Sat
1 stopDelta
4h 56mJFK-ORD
5/14Tue
nonstopDelta
2h 26mORD-JFK
$491

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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.
5/21Tue
nonstopAmerican Airlines
2h 40mEWR-ORD
$190
6/18Tue
nonstopUnited Airlines
2h 50mBOS-ORD
$209
5/11Sat
nonstopAmerican Airlines
2h 40mEWR-ORD
$215
5/11Sat
nonstopDelta
2h 51mJFK-ORD
$223
5/16Thu
nonstopAmerican Airlines
2h 35mLGA-ORD
$227
5/3Fri
nonstopDelta
2h 59mJFK-ORD
$229
5/10Fri
nonstopAmerican Airlines
4h 12mSEA-ORD
$244
6/4Tue
nonstopUnited Airlines
2h 38mLGA-ORD
$249
6/4Tue
nonstopUnited Airlines
2h 35mEWR-ORD
$255
7/21Sun
nonstopUnited Airlines
2h 46mBOS-ORD
$255
5/11Sat
1 stopDelta
6h 22mJFK-ORD
$264
5/16Thu
1 stopAmerican Airlines
4h 53mEWR-ORD
$264
5/16Thu
1 stopAmerican Airlines
3h 56mLGA-ORD
$267
6/11Tue
1 stopUnited Airlines
4h 35mLGA-ORD
$268
5/4Sat
1 stopDelta
5h 12mJFK-ORD
$273
5/8Wed
nonstopAmerican Airlines
2h 35mLGA-ORD
$279
6/18Tue
1 stopDelta
6h 25mBOS-ORD
$282
5/8Wed
1 stopAmerican Airlines
3h 56mLGA-ORD
$288
5/3Fri
nonstopUnited Airlines
2h 37mEWR-ORD
$289
5/4Sat
nonstopDelta
2h 51mLGA-ORD
$289

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Flights to Chicago

Return flight deals:

Chicago - United States

Cabin classes:

$274
$293
$217
$38

Browse origins: