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Find First Class Flights to Chicago

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Sun 6/16
Sun 6/23

Good to Know - First Class Flights to Chicago

Low season

January

High season

May

Average price round-trip

$2,550

Good deal round-trip

$762

Good deal one-way

$259
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 5% 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.
  • To get a below average price, try to book at least 1 week in advance of your departure date.
  • 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 6039 reviews
8.1Comfort
8.3Boarding
8.7Crew
7.8Entertainment
7.3Food
Airline reviews

Our flight to Oakland was great bc the plane was new but it was delayed by 15min not bad at all. Over all it was an 8/10

8.0 ExcellentLarry, May 2024OAK - ONT
Read more about Southwest reviews

Our flight to Oakland was great bc the plane was new but it was delayed by 15min not bad at all. Over all it was an 8/10

Our first flight was so delayed that we had 10 mins to board the next one. We requested if the flight attendant could allow us off there plane first and they denied our request even though I have seen this done before. Luck was on our side that we didn’t miss our next flight.

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.

C Am handicapped and couldn't get help with my luggage.

Southwest is going downhill. I'm more apt to fly other airlines now. And I'd appreciate it if your gate agents didn't invent non-existent laws. If Southwest is having issues getting flight crews, you need to go out of your way to accommodate passengers instead of saying it's weather related and not in your hands. We can all see the other carriers are getting their planes off the ground and to/from the cities/regions you claim are weather-impacted.

Southwest is a discount airline. I get it. You take the (usually) good pricing with the bad (cramped). But Southwest is becoming more and more like the cut-rate airlines *cough* Spirit *cough*. It used to actually be a fun experience. e.g. paying for WiFi is bad enough - having to pay for it on each leg of a flight is ridiculous. Yes, I've seen your numbers that it only "impacts a small percentage", but you and I both know that is misleading at best. While I used to try to fly SW exclusively when flying domestically, now I'll look elsewhere very frequently and price being equal (or close) I'm going to the other carriers.

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

I enjoyed the leg room at my seat, but I was in an exit row.

Why do you ask about food when only a snack is served? Actual food needs to be bought.

There was an older male crew member that was very rude to me when doing the last checks before pulling back from the terminal. There is a polite way to tell someone to put their bag under the seat. It was Mother’s Day and my mom has recently passed so it was a tough morning for me in general. There was no need to make for the snide remark “ I don’t know how many times we have said this already” as you walked away. I had held it together all morning and this interaction brought me to tears. love Alaska Airlines and this is the first time I’ve had a negative experience.

Alway a a breeze! And great mountain views on left side of plane during entire flight!

another delayed flight. no one at the desk kept us updated. we found out by an email as the desk was not even staffed up to expected takes off

They canceled my flight going back to SF after I was at the airport. Wanted me to take a flight 14 hours later. Not a happy camper.

Service was excellent. Staff at check in cleared hurdles for me so I could travel with my service animal.

Flight cancelled an hour before takeoff due to "unscheduled maintenance". New flight makes me have to wait for 5 hours in the airport, at a gate totally on the other side of where I'm at, requiring me to take a tram to get from the N terminal, to the C terminal. After waiting for 5 hours I'm informed my new flight is no longer at the gate I'm at, but instead is back in the N terminal where I was previously.

Delayed an hour and sat without updates. Ended up an hour late to destination

The flight was decent again if there was a place that you could put crying children that would be great. Or maybe make a rule against allowing infants on the plane.

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.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Absolutely nothing flight was cancelled and delayed for 2 days. Barely a heads up I want a full refund

The plane from SNA wouldn’t start after 5 tries. The team gave me an option of flying direct from LAX and giving me a Lyft ride there! Perfect!

Best airline! Always friendly and welcoming. Skyclub was great and loved the fast free wifi on board. I also love that you can pre-order your meal on the app!

Atlanta boarding crew at gate were filled with arrogance and were disrespectful. In flight crew showed indifference to the needs of passengers. This is about the flight from ATL to BDL.

Boarding was somewhat chaotic. Unable to evaluate crew or food/drink because captain kept them seated due to turbulence. Have no idea if entertainment was offered.

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

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

Delayed departure. Delayed after landing pulling into gate. Delay due to sky bridge malfunction

Great. Loved that there was WiFi on flight to keep in touch and excellent service of beverages and snacks.

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Terrible. Flight was cancelled due to the weather in the east and sout east(florida). Did not get any compesation of any kind. According to them, it was not under their control so I lost all the money paid for the 2 fairs from Raleigh, NC to Orlando, Fl.

great flight. Pilot was communicative, flight attendants were excellent. Really nice experience except my tv didn’t work.

Overall, the flight was better than the flight I took to go to Florida, which had a bunch of problems. The crew is really nice and the plane was new so it had a small problem when we were on the runway, but the flight itself was great. They even made some time back up, which is always a good thing.

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

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.

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.

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

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.
6/15Sat
nonstopDelta
2h 58mJFK-ORD
7/24Wed
nonstopDelta
2h 41mORD-JFK
$433
7/17Wed
nonstopUnited Airlines
2h 50mBOS-ORD
7/21Sun
nonstopUnited Airlines
2h 22mORD-BOS
$433
6/17Mon
nonstopAmerican Airlines
2h 34mLGA-ORD
6/18Tue
nonstopAmerican Airlines
2h 13mORD-LGA
$440
6/15Sat
nonstopDelta
3h 01mJFK-ORD
7/24Wed
nonstopDelta
2h 41mORD-JFK
$443
6/6Thu
nonstopDelta
2h 55mBOS-ORD
6/9Sun
nonstopDelta
2h 28mORD-BOS
$447
8/7Wed
nonstopUnited Airlines
2h 36mDFW-ORD
8/21Wed
nonstopUnited Airlines
2h 37mORD-DFW
$447
6/17Mon
1 stopAmerican Airlines
4h 54mLGA-ORD
6/18Tue
nonstopAmerican Airlines
2h 13mORD-LGA
$450
7/18Thu
nonstopDelta
2h 59mBOS-ORD
7/21Sun
nonstopDelta
2h 26mORD-BOS
$457
8/7Wed
nonstopUnited Airlines
2h 36mDFW-ORD
8/21Wed
1 stopUnited Airlines
6h 02mORD-DFW
$457
6/15Sat
nonstopDelta
2h 58mJFK-ORD
7/26Fri
nonstopDelta
2h 41mORD-JFK
$463
6/15Sat
nonstopDelta
3h 01mJFK-ORD
6/25Tue
nonstopDelta
2h 21mORD-JFK
$467
8/23Fri
nonstopUnited Airlines
2h 43mBOS-ORD
8/26Mon
nonstopUnited Airlines
2h 26mORD-BOS
$467
5/29Wed
1 stopUnited Airlines
4h 43mDFW-ORD
5/31Fri
nonstopUnited Airlines
2h 33mORD-DFW
$468
9/16Mon
nonstopUnited Airlines
2h 48mBOS-ORD
9/18Wed
nonstopUnited Airlines
2h 29mORD-BOS
$474
10/2Wed
nonstopDelta
2h 47mJFK-ORD
10/4Fri
nonstopDelta
2h 47mORD-JFK
$476
5/30Thu
1 stopUnited Airlines
4h 36mEWR-ORD
5/30Thu
nonstopUnited Airlines
2h 30mORD-EWR
$477
6/6Thu
nonstopDelta
2h 53mBOS-ORD
6/9Sun
nonstopDelta
2h 28mORD-BOS
$478
8/28Wed
nonstopDelta
2h 35mLGA-ORD
8/30Fri
nonstopDelta
2h 16mORD-LGA
$479
5/27Mon
nonstopDelta
2h 42mJFK-ORD
6/1Sat
1 stopDelta
7h 02mORD-JFK
$482
6/17Mon
1 stopAmerican Airlines
4h 54mLGA-ORD
6/18Tue
1 stopAmerican Airlines
3h 43mORD-LGA
$482

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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.
9/5Thu
nonstopDelta
2h 50mBOS-ORD
$194
11/13Wed
nonstopDelta
3h 05mJFK-ORD
$200
6/18Tue
nonstopDelta
2h 44mJFK-ORD
$204
9/5Thu
nonstopUnited Airlines
2h 48mBOS-ORD
$204
5/26Sun
nonstopDelta
2h 51mJFK-ORD
$219
5/25Sat
nonstopDelta
2h 51mJFK-ORD
$229
6/5Wed
1 stopUnited Airlines
4h 50mBOS-ORD
$239
5/25Sat
nonstopDelta
2h 57mLGA-ORD
$240
7/22Mon
nonstopUnited Airlines
2h 30mDFW-ORD
$244
6/5Wed
nonstopDelta
2h 44mLGA-ORD
$249
8/14Wed
nonstopDelta
2h 43mJFK-ORD
$254
8/7Wed
nonstopUnited Airlines
2h 37mEWR-ORD
$254
6/18Tue
nonstopUnited Airlines
2h 35mEWR-ORD
$257
8/13Tue
nonstopUnited Airlines
2h 37mEWR-ORD
$259
5/31Fri
nonstopUnited Airlines
2h 38mLGA-ORD
$259
6/5Wed
nonstopDelta
2h 42mJFK-ORD
$264
7/19Fri
nonstopAmerican Airlines
2h 49mEWR-ORD
$264
5/25Sat
1 stopUnited Airlines
5h 05mDFW-ORD
$264
8/14Wed
1 stopUnited Airlines
4h 10mEWR-ORD
$268
6/11Tue
nonstopUnited Airlines
2h 11mDCA-ORD
$270

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Flights to Chicago

Return flight deals:

Chicago - United States

Cabin classes:

$326
$296
$246
$37

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