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Find First Class Flights to Chicago

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Sun 6/9
Sun 6/16

Good to Know - First Class Flights to Chicago

Low season

January

High season

May

Average price round-trip

$3,054

Good deal round-trip

$568

Good deal one-way

$311
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 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.
  • 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 6069 reviews
8.1Comfort
7.8Entertainment
8.7Crew
8.3Boarding
7.3Food
Airline reviews

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.

2.0 MediocreDavid, May 2024COS - MDW
Read more about Southwest reviews

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!

The flight itself was good. Delays were the problem. Original flight was scheduled for 8:10 pm. Got notifications all day -- actual time is 8:40; then 8:25; then 8:35; then 8:45. Then once I get through security, it's actually 9:35.

Crew was great but because of fog they diverted us to Ontario instead of our Santa Barbara destination. Instead of cancelling the flight as soon as we landed in Ontario, they instead held us in Ontario for almost 4 hours before cancelling the flight. I had to rent a car in Ontario to get back to ventura on time to get an elderly relative his medication and take over his caretaking… otherwise if I had taken the buses you offered from Ontario I wouldn’t have even arrived to Santa Barbara till at least midnight (according to southwest airlines employees at Ontario), and then would have had to drive back down to ventura. At least renting the car I could get up to ventura by 10 pm to take care of my loved one.

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

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.

Everything was fine -- on time, clear, clean. I don't want to pay extra for in-flight wi-fi

The flight was delayed because the pilots had not arrived on their previous flight yet. The flight was 100% full so it was pretty crowded. I miss having the screens on the back of the seats. It would be great if the Alaska planes had the clip so you can put your phone or tablet on the back of the seat in front of you to not strain your neck. Everything else was very smooth.

Boarded the plain and had to wait 1 hour for crew Captain to arrive from another flight

It was fine since it ensure we went to our destination in time.

I bought the cheapest ticket. No meal, no checked luggage so I didn't expect much and was surprised by how good the flight and service was. Alaska is now my favorite airline.

No entertainment, food was cookies & juice,water, soda or coffee.

My baggage was in another flight, anit was delayed for one hour.

Everything went smoothly. I didn’t like that when I booked in the main cabin my wife and I weren’t seated together. One would think when booking on an option that allows picking your seat. They would put you and your travel partner together. Had to call to get it sorted. They did fix.

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.

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.

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

40 minute delay before take off after boarding flight. Bright lights throughout night flight due Issues with light panels. In flight Entertainment nonfunctional

Everything was good except for deplaning in NY. Took way too long!!

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.
5/25Sat
nonstopDelta
2h 51mJFK-ORD
5/31Fri
nonstopDelta
2h 18mORD-JFK
$432
6/15Sat
nonstopDelta
2h 45mJFK-ORD
7/24Wed
nonstopDelta
2h 38mORD-JFK
$443
5/22Wed
nonstopDelta
2h 42mJFK-ORD
5/29Wed
nonstopDelta
2h 33mORD-JFK
$448
6/15Sat
nonstopDelta
2h 45mJFK-ORD
7/26Fri
nonstopDelta
2h 38mORD-JFK
$453
6/16Sun
nonstopUnited Airlines
2h 50mBOS-ORD
6/21Fri
nonstopUnited Airlines
2h 35mORD-BOS
$459
5/27Mon
nonstopDelta
2h 42mJFK-ORD
5/28Tue
nonstopDelta
2h 33mORD-JFK
$467
6/3Mon
nonstopAmerican Airlines
2h 43mLGA-ORD
6/4Tue
nonstopAmerican Airlines
2h 01mORD-LGA
$471
6/15Sat
nonstopDelta
2h 58mJFK-ORD
7/23Tue
nonstopDelta
2h 14mORD-JFK
$472
5/27Mon
nonstopDelta
2h 42mJFK-ORD
5/29Wed
1 stopDelta
4h 48mORD-JFK
$476
5/28Tue
nonstopDelta
2h 51mJFK-ORD
5/29Wed
1 stopDelta
4h 48mORD-JFK
$481
6/16Sun
1 stopDelta
5h 01mBOS-ORD
6/21Fri
nonstopDelta
2h 28mORD-BOS
$482
6/16Sun
nonstopDelta
2h 45mJFK-ORD
7/24Wed
nonstopDelta
2h 14mORD-JFK
$483
6/6Thu
nonstopAmerican Airlines
2h 55mBOS-ORD
6/9Sun
1 stopAmerican Airlines
4h 05mORD-BOS
$485
6/6Thu
nonstopAmerican Airlines
2h 55mBOS-ORD
6/9Sun
1 stopAmerican Airlines
4h 05mORD-BOS
$486
6/10Mon
nonstopUnited Airlines
2h 44mBOS-ORD
6/14Fri
nonstopUnited Airlines
2h 35mORD-BOS
$489
5/21Tue
nonstopUnited Airlines
2h 53mBOS-ORD
5/26Sun
nonstopUnited Airlines
2h 31mORD-BOS
$492
7/22Mon
nonstopDelta
3h 01mJFK-ORD
8/16Fri
nonstopDelta
2h 47mORD-JFK
$493
5/27Mon
nonstopDelta
2h 42mJFK-ORD
6/1Sat
nonstopDelta
2h 18mORD-JFK
$497
6/18Tue
nonstopDelta
2h 44mJFK-ORD
7/22Mon
nonstopDelta
2h 14mORD-JFK
$505
6/6Thu
nonstopAmerican Airlines
2h 55mBOS-ORD
6/9Sun
nonstopAmerican Airlines
2h 26mORD-BOS
$506

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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
$190
10/25Fri
nonstopDelta
3h 05mJFK-ORD
$205
5/27Mon
nonstopDelta
2h 42mJFK-ORD
$209
6/26Wed
nonstopAmerican Airlines
2h 34mLGA-ORD
$209
5/25Sat
nonstopDelta
2h 51mJFK-ORD
$219
6/4Tue
nonstopDelta
3h 02mBOS-ORD
$219
6/4Tue
1 stopUnited Airlines
4h 50mBOS-ORD
$223
6/2Sun
nonstopAmerican Airlines
2h 52mBOS-ORD
$226
7/19Fri
nonstopAmerican Airlines
2h 55mBOS-ORD
$227
6/3Mon
nonstopUnited Airlines
2h 50mBOS-ORD
$230
6/6Thu
nonstopAmerican Airlines
2h 34mLGA-ORD
$232
5/16Thu
nonstopUnited Airlines
2h 53mBOS-ORD
$234
7/10Wed
nonstopAmerican Airlines
2h 37mEWR-ORD
$240
7/9Tue
nonstopDelta
2h 48mLGA-ORD
$240
6/6Thu
1 stopAmerican Airlines
4h 54mLGA-ORD
$241
7/12Fri
nonstopDelta
2h 50mLGA-ORD
$244
7/25Thu
nonstopDelta
2h 57mBOS-ORD
$245
6/2Sun
1 stopAmerican Airlines
5h 27mBOS-ORD
$250
7/20Sat
nonstopAmerican Airlines
2h 56mBOS-ORD
$251
5/21Tue
nonstopDelta
2h 51mJFK-ORD
$254

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Flights to Chicago

Return flight deals:

Chicago - United States

Cabin classes:

$333
$301
$219
$38

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