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Find First Class Flights to Chicago

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Mon 6/3
Mon 6/10

Good to Know - First Class Flights to Chicago

Low season

January

High season

May

Average price round-trip

$1,265

Good deal round-trip

$428

Good deal one-way

$182
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 6092 reviews
7.3Food
7.8Entertainment
8.3Boarding
8.7Crew
8.1Comfort
Airline reviews

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.

6.0 GoodTobin, Apr 2024PHX - BUR
Read more about Southwest reviews

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.

Boarding was quick. The flight itself was good. However, no charging ports for cell phones. Also, the food provided was just a few snacks. For a 5-hr flight, I would expect at least a sandwich.

Landing was kinda fast and my ears were plugged for days after.

Healthier snack would be much appreciated. Love traveling on Southwest!

We sat on the tarmac for 2 hours waiting in line to be de-iced. The flight is 1.5 hours, so we spent more time tied to our seats for no reason than actually flying.

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

Boarding was well explained and smooth. The flight was short, so there was no time for snacks. They did offer water or juice, though.

Our flight to Vegas was delayed by almost two hours - I appreciated the updates but it was a bummer of a start to a celebratory trip. The delays meant we missed our dinner reservations we made a month ago so that was disappointing. Once we got to the gate, though, the crew did all they could to make up for the lost time and to keep it efficient and enjoyable, so I appreciate their efforts!!

As always it was a pleasure to fly on southwest.

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.

The maintenance delay was seemingly handled very poorly... Little to no information was provided to the passengers sitting on board for an extended period of time. On a brighter note, at least the cabin crew (flight attendants) did the best they could. They seemingly were provided very little information with regards to the delay. Unless absolutely beyond my control, I can’t imagine buying a ticket on Alaska airlines again, based on this and a previous experience my wife recently had, along with complaints overheard from other passengers.

The only issue was in the wheelchair waiting area before we got on the plane. They seemed very disorganized. Everyone we encountered after that was great! We loved Cassandra at check-in. She was awesome. The flight attendants were wonderful too! The lady helping with the waiting wheelchair when we got off the plane was awesome too!

They canceled the flight 30 minutes prior to departure without any heads up.

Expect to get miles for us having to miss our first planned flight due to them waiting on passengers that decided to be late to the airport.

Up on arrival, due to twisted ankle, I wasn’t able to walk. Requested for a wheelchair. They immediately asked for it. After 10 minutes wait a young man named Carlos picked me up at the gate, got my baggage and took me to the pick up area. It was a great service. Thanks Alaska Air line

Once I was in my seat, it wasn't as comfortable. It was very tight (width wise).

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

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.

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?

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

Wasn’t on the flight- again. Bad weather in Halifax and I was in an accident. What a poor experience to have to pay for all this flight and not be on it

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.
7/4Thu
nonstopDelta
2h 58mJFK-ORD
7/10Wed
nonstopDelta
2h 14mORD-JFK
$389
7/4Thu
nonstopDelta
2h 58mJFK-ORD
7/11Thu
nonstopDelta
2h 14mORD-JFK
$399
6/18Tue
nonstopDelta
2h 44mJFK-ORD
7/20Sat
nonstopDelta
2h 38mORD-JFK
$441
5/25Sat
nonstopDelta
2h 51mJFK-ORD
5/29Wed
1 stopDelta
4h 48mORD-JFK
$450
7/4Thu
nonstopDelta
2h 58mJFK-ORD
7/9Tue
nonstopDelta
2h 14mORD-JFK
$451
7/4Thu
nonstopDelta
2h 58mJFK-ORD
7/12Fri
nonstopDelta
2h 14mORD-JFK
$452
6/3Mon
nonstopDelta
2h 55mBOS-ORD
6/10Mon
nonstopDelta
2h 28mORD-BOS
$454
8/28Wed
nonstopUnited Airlines
2h 48mBOS-ORD
8/30Fri
nonstopUnited Airlines
2h 29mORD-BOS
$463
5/28Tue
nonstopDelta
2h 51mJFK-ORD
5/31Fri
nonstopDelta
2h 18mORD-JFK
$472
9/17Tue
1 stopUnited Airlines
4h 46mBOS-ORD
9/24Tue
1 stopUnited Airlines
6h 14mORD-BOS
$478
5/25Sat
1 stopUnited Airlines
5h 10mBOS-ORD
5/28Tue
nonstopUnited Airlines
2h 31mORD-BOS
$480
7/4Thu
nonstopDelta
2h 45mJFK-ORD
8/8Thu
1 stopDelta
4h 22mORD-JFK
$481
6/15Sat
1 stopAmerican Airlines
5h 30mLGA-ORD
6/16Sun
1 stopAmerican Airlines
5h 28mORD-LGA
$482
8/28Wed
1 stopUnited Airlines
4h 46mBOS-ORD
8/30Fri
nonstopUnited Airlines
2h 29mORD-BOS
$482
6/19Wed
nonstopDelta
2h 45mJFK-ORD
7/20Sat
nonstopDelta
2h 38mORD-JFK
$483
6/3Mon
nonstopAmerican Airlines
2h 56mBOS-ORD
6/10Mon
1 stopAmerican Airlines
4h 05mORD-BOS
$485
5/28Tue
nonstopUnited Airlines
2h 35mLGA-ORD
5/31Fri
nonstopUnited Airlines
2h 21mORD-LGA
$487
5/28Tue
nonstopUnited Airlines
2h 50mBOS-ORD
6/2Sun
nonstopUnited Airlines
2h 20mORD-BOS
$492
7/1Mon
nonstopDelta
2h 45mJFK-ORD
8/6Tue
nonstopDelta
2h 32mORD-JFK
$493
6/26Wed
1 stopUnited Airlines
5h 38mDFW-ORD
6/29Sat
nonstopUnited Airlines
2h 33mORD-DFW
$493

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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
5/21Tue
nonstopAmerican Airlines
2h 40mEWR-ORD
$220
6/5Wed
nonstopAmerican Airlines
2h 34mEWR-ORD
$221
6/5Wed
1 stopUnited Airlines
4h 50mBOS-ORD
$223
6/22Sat
nonstopUnited Airlines
2h 36mDFW-ORD
$230
5/21Tue
nonstopAmerican Airlines
2h 35mLGA-ORD
$232
6/22Sat
1 stopUnited Airlines
5h 05mDFW-ORD
$239
5/21Tue
1 stopAmerican Airlines
3h 56mLGA-ORD
$241
5/25Sat
nonstopUnited Airlines
2h 37mLGA-ORD
$244
5/14Tue
nonstopUnited Airlines
2h 53mBOS-ORD
$245
6/5Wed
nonstopDelta
2h 42mJFK-ORD
$247
6/5Wed
nonstopUnited Airlines
2h 38mLGA-ORD
$249
5/14Tue
nonstopDelta
2h 55mBOS-ORD
$249
6/18Tue
nonstopDelta
2h 44mJFK-ORD
$252
5/21Tue
nonstopDelta
2h 51mJFK-ORD
$253
6/5Wed
nonstopUnited Airlines
2h 35mEWR-ORD
$255
6/10Mon
nonstopAmerican Airlines
2h 37mEWR-ORD
$261
6/6Thu
nonstopAmerican Airlines
2h 34mEWR-ORD
$263
5/25Sat
1 stopUnited Airlines
4h 51mLGA-ORD
$269
7/24Wed
nonstopUnited Airlines
2h 13mDCA-ORD
$270

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Flights to Chicago

Return flight deals:

Chicago - United States

Cabin classes:

$274
$293
$219
$38

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